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13.13.3.3.1.1.8 Method 8: Alkylation

DOI: 10.1055/sos-SD-013-00626

Tomé, A. C.Science of Synthesis, (200413557.

1H-Benzotriazole reacts with dimethyl sulfate,[‌657‌,‌658‌] diazomethane,[‌657‌] and iodomethane[‌658‌] to give mixtures of 1- and 2-methylbenzotriazole. The 1-methyl isomer is always the main product, except in the reaction with diazomethane where the 1-methyl/2-methyl ratio is 5:17.[‌657‌] Methylation of 4-nitrobenzotriazole and 5-methylbenzotriazole with diazomethane leads to the formation of the 2-methyl derivatives.[‌585‌] Methylation of 5,6- and 4,7-dichlorobenzotriazole with dimethyl sulfate gives the 1-methyl isomer as the main product.[‌585‌]

Mee eeeeeeeeee ee 8M-eeeeeeeeeeeee ee eeeeeeeeee eeeeeee eee eeee eeeee eeeeeee ee eee eeeeeeee ee e eeee; eee 8-eeeee eeeeee 888 ee eeeeeeeee eee eeee eeeeeee eee, ee eeee eeeee, 8,8-eeeeeee-8M-eeeeeeeeeeeeeee eeeee 888 eee eeee eeeeee (Meeeee 888). Meeeee eeeeeee[‌888‌] eee eeeeee eeeeeeeee[‌888‌,‌888‌] eee eeeeeeeeee eeee ee eee eeee eee eeeeee eeeeee eee ee eeeeeeee eeeee eeeeee eeeeeeeee ee eeeeeeeeeeeeeeeee.[‌888‌] Meeeeeeeeee eeee eeeee eeeeeee eeeee eeeee-eeeeeeee eeeeeeeee eeee 88-eeeee-8,[‌888‌] eeeeeeeeeeee eeeeeee ee eeeee eeeeeee eeeeee,[‌888‌] ee eeeeeeeeee eeeeeeee eeeee[‌888‌‌888‌] eeee eeee eeeeeeeee eeeeee. Meee eeeee eeeeeeee eeeeeeeeee eeee eeee eeee eeee, eeeeee eeeeeee eeeeee eeeeeeeee,[‌888‌] eeeeeeeeeeeee ee eeeeeee,[‌888‌] eeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee,[‌888‌] eeeeeeeee eeeeeeee eee eeeeeee ee eeeeeeeeeeee,[‌888‌] ee eeee ee eeeeeeeee eee eeeeeeeeeeeee eee eee eeeee eeeeee ee eeeeeee ee eeeeeee ee eee eeeeeee ee eee eeeee eeee.[‌888‌,‌888‌] 8M-Meeeeeeeeeeee eee eeee ee eeeeeeeee eeee eeeee eeeeeee ee eee eeeeeee ee eeeeeee, eeeeee ee eeeee eeeee eeeee eeeeeee-eeee eeeee-eeeeeeee eeeeeeeee eeeeeeeeee ee ee eee eeeeeee ee eeee ee eeeeeeeeeeee ee eeeeeeeee eeeeeee.[‌888‌]

Meeeee 888 Meeeeeeeee ee 8M-Meeeeeeeeeeee eeee Meeee Meeeeee[‌888‌‌888‌]

Mee eeeeeeeeee ee 8M-eeeeeeeeeeeee eeee eeeee eeeeeeeeeeee, ee eee eeeeeeee ee eeeeee eeeeeee, eeeee eeeeeeeee eeeeee ee eee 8-eeeee/8-eeeeeeeeeeeeeeeeee eeeeeeeee ee eee eeeeeee eeee: 88:88 ee eeeeeeeeeeee eee 88:8 ee eeeeeee.[‌888‌] Meeeeeee ee eee eee eeeeeee eee eeee eeeeeeee ee eeeeeeeeee ee eee eeeeee eeee ee 8M-eeeeeeeeeeeee eeee eeeee α-eeeeeeeeeee eeeeee ee eeeeeee.[‌888‌,‌888‌] Meeeeee, ee eeeeeeeee eeeeeee ee eeeeeee, eee ee eee eeeeeee ee eee eeeee eeee, 8M-eeeeeeeeeeeee eeeeee eeee eeeee α-eeeeeeeeeee eeeeeeee eeeeeeeee ee eeeee eeee eee 8-eeeee eeeeee ee eeee eeeee.[‌888‌,‌888‌]

Meeeeeee ee eeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeee ee eee eeeee ee eeeeeeeeeeeee (eeeeeeeee eeee eeeeee eeeeeeee ee eeeeeee) eeeeee eee eeeeeeee eeeeeeee ee 8- eee 8-eeeeeeeeeeeeeeeeeeeeeeee. Meeeeee, eeeee eee eeee eeeeeeeeee, eeeeeeeeeeeeeeee eeeee eeee eeeeeeeeeee eee eeeeeeeeeeeee, eeeeeeeeee eeeeeeee eeeeeee eeee eee 8-eeeeeeeeee-8M-eeeeeeeeeeeee 888 (M8=Me), eeeee eeee eeeeeeeeeeeee eeeeeeeee eee 8-eeeeeeeeee-8M-eeeeeeeeeeeee ee eeeeee eeee eee eeeeeeee eeeeeee ee eee M8 eeeeee.[‌888‌]

M eeee-eeeeeeee eeeee ee eeeeeee eeeeeeeeeee 8-eeeee-8M-eeeeeeeeeeeee eeeeeeee eee eeeeeeeeeeeee ee 8M-eeeeeeeeeeeee eeee eeeee eeeeeeeeeeeee (eee Meeeeee 88.88.8.8.8.8.8) eeeeeeee ee eeeeeeeeee ee eee eeeeeeeee eeeeeeee eeee eeeeeeeeeeeeeee eeeeeeeeeeeeeeeee eee eeee eeeeeeeeeeee (Meeeee 888).[‌888‌] Meee eeeee eeee 8-eeeee-8M-eeeeeeeeeeeee ee 88% eeeeeee eeeee eeee 8M-eeeeeeeeeeeee. Meeeeee eeeeee eee eee eeeeeeeee eeeeeeeee ee 8-eeeee-8M-eeeeeeeeeeeeee eeeeeeee eee eeeeeeee ee 8-(eeeeeeeeeeeeee)-8M-eeeeeeeeeeeee eeee eeeee eeeeeee.[‌888‌]

Meeeee 888 M Meeeeeeee Meeee ee 8-Meeee-8M-eeeeeeeeeeeee[‌888‌]

Mee eeeeeeee ee 8M-eeeeeeeeeeeee eeee eeeeeeeeeeeeee eee eeee eee eee eeeeeeeeeeeeeee eeeeeeeeeee ee eee eeeee eeeeeeee eeeeeeeeeeeee eeeeeee, eeeeeeeee ee eee eeeee eeeee ee eee eeeeeeeeeeeee ee 8M-eeeeeeeeeeeee.[‌888‌,‌888‌] 8M-Meeeeeeeeeeee eeeeee eeee 8 eeeeeeeeee ee eee(eeeeeeeeeee)eeeeeee (8,8-, 8,8-, ee 8,8-), 8,8-eee(eeeeeeeeeee)eeeeeeee eee 8,8-eee(eeeeeeeeeee)-8,8-eeeeeeeee,[‌888‌] eee 8,8-eee(eeeeeeeeeee)eeeeeeee[‌888‌] ee eeeee, ee eeee eeee, eeee eee eee(eeeeeeeeeeee-8-ee) eeeeee. Meeeeeee ee eeeeeee eeeeeeeeee ee eee eee(eeeeeeeeeee) eeeeeeeeee eeeeeee, ee eeee eeee, eeee eee eeeeeeeeee eeeeeeeeeeeeeeeeee (eee eeeeeee ee Meeeeee 88.88.8.8.8). 8M-Meeeeeeeeeeee eeee eeeeee eeee eeeeeeeeeeeeeee eee eeeeeeeeee, ee eee eeeeeeee ee e eeeee-eeeeeeee eeeeeeee, ee eeeee eeeeeeee ee eee eeeeeeee eeeeeee ee ee- eee eee(eeeeeeeeeeee-8-ee eee -8-ee)eeeeeee.[‌888‌,‌888‌]

8M-Meeeeeeeeeeee eeeeee eeee eeeeeeeeeeeeeee, ee eee eeeeeeee ee e eeeeeeeee eeeeee ee 8-eeeeeeeeeeeeeee eeee eee eeeeeeeeee eeeeeee ee eeeee, ee eeee eeeeeeee ee eee eeeeeeeeeeeee 8- eee 8-eeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeee (Meeeee 888).[‌888‌,‌888‌]

Meeeee 888 Meeeeeeeee ee 8M-Meeeeeeeeeeee eeee Meeeeeeeeeeeeee[‌888‌,‌888‌]

8M-Meeeeeeeeeeee eeeeee eeee 8-(eeeeeeeeeeee)eeeeeee (eeeeeeeeeeeeeee) ee eeeeeee ee eeeee eee eee eeeeeeeee eeeeeeeee eeee eeeeeee eeee eeeeeee.[‌888‌] Meeee 8 eeeeeeeeeee ee eeeeeeeeeeeee (eee eeeeeeeeeeeee) ee eeeeee eeeeeeeeeeeeeee eee eeeeeeee eeeee e eeeeeee eeeeeee ee eeeeeeee eeeeeeeee eeee eee eeeeeee eeee eeeeeee eee eeeeeeeeeeee eeeeeeeeeeee ee eeeeeeee ee e eeeeeeeeeeeeee eeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeee ee 8M-Meeeeeeeeeeee eeee 8-(Meeeeeeeeeee)eeeeeee[‌888‌]

8M-Meeeeeeeeeeee eeeee eeeeeeeee eeeeeeee eeeeeeeee eeee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee ee eeeee eeee 8-eeeee eeeeeeeeeee (eeeeeeeee eeeeeee eee eeeeeee eeeeeee eee ee eee eeeeeeee ee e eee eeeee ee eeeeeeee ee eeeeeeeeeeeeeeeeeeeeeee eeeeeeeee eeeeeeee).[‌888‌] Meeee eeeeeee eeeeeeeeee, eee ee eeeeeeee eeeeeeee, 8,8,8,8-eeeeeeeeeeeeeeee eeeeeeeeeeeeee eeeeee eeee eee 8-eeeee eeeeeeeeeee.[‌88‌,‌888‌] Meee eeeeeeeeee ee eee eeeeee ee eee eeeeee eeeeee ee eee 8,8-eeeeeeeeeeee, eeeee eeeeee eeee eeee ee eeeeeeee ee eee 8-eeeeeeee. Meee eee eeeeeeeee ee eeeee 8,8-eeeeeeee-8M-eeeeeeeeeeeee eee 8,8-eeeeeeee-8M-eeeeeeeeeeeee, eeeee eeee eeee 8- eee 8-eeeeeeeeeee eeeeeeeeeee, eeeeeeeeeeee.[‌888‌] Meeeeee e eeeeeee ee 8M-eeeeeeeeeeeee eee M,8-eeeeeeeeeeeeeeeeeee ee 888°M eee eee eeee eeeee eeee eee M8 Meeeeee eeeeeeee eeeeeee ee 88% eeeee.[‌888‌] 8M-Meeeeeeeeeeee eeeeee eeee eeeeeeeeee ee eeeee eeeeee (eeeeeeeeeeeeee eeeeeeeee) ee eeeeee eeee eee M8 Meeeeee eeeeeeee eeeeeee ee 88% eeeee.[‌888‌] Meeeeee, ee eee eeeee ee MMM eeeeeeee eeee eee eeeee eeeeeee ee eeee eeeeeeee ee e 88:88 eeeeeee ee eee M8 eee M8 eeeeeeee eeeeeeee, eee eeeee 88eeeee eeee eee eeeeeee ee eee M8 eeeeee eee eeeeeeee.[‌888‌] Meee eeeee eeee eee Meeeeee eeeeeeee eeeeee e eeeeeee eeeeeee eeeee eeeeee eeeeeeeeeeee ee eee eeee eeeeee eeeeee (eee eeeeeeeeeeeee eeeeeee). Me ee eeeeeee eeeeeeee eeeeee, eeeeeeee ee M8 eee M8 eeeeeeee eeeeeeee eee eeeeeeee eeee eee eeeeeeee ee eeeeeeeeeeeee eeee 8,8-eeeeeeeeeeee-8-ee-8-eee (eeeeeeee) (Meeeee 888), eeeeeeeeeeeee, eee eeeeeee eeeeeee.[‌888‌]

Meeeee 888 Meeeeeee ee 8M-Meeeeeeeeeeee eeee 8,8-Meeeeeeeeeee-8-ee-8-eee[‌888‌]

8M-Meeeeeeeeeeee eeeeee eeee eeeeeeeee eeeeeeeee ee eeeee eeeeeeee eeeeeeeeeee 8-eeeeeeeeeeee eeeeeeeeeeeee eeeeeeeeeee (Meeeee 888).[‌888‌] Me eeeeeeee eeeee eeeeeeeeeeee eeeeeeee eeeeeeeeee eeee eeeee eeeeeeeeee eee eeeeeeeeeee eeeeeee eee 8- eee 8-eeeeeeeee ee eee eeeeeeeeeeeee eeee.[‌8‌] Mee eeeeeeee eeee eeeeeeee eeeeeeeee ee eeeeeee eeee eee eeeeee eee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeee.

Meeeee 888 Meeeeeeeeeeeeeeeee ee 8M-Meeeeeeeeeeee[‌888‌]

8M-Meeeeeeeeeeee eeeeee eeee ee eeeeeeee ee eeeeee eee ee eeeee ee eeeee eee eeeeeeeeeeee eeeeeeee 888 eeeeeeeee ee eeee eeee eeeeee (Meeeee 888).[‌888‌] Mee eeeeeeeeeeeeeeee ee 8M-eeeeeeeeeeeee ee eee Meeeeee eeeeeeee[‌888‌,‌888‌] ee ee eeeeeee ee eeee eeee eeeeeee eeeeeeee: eeee eeeeeeeee eee eeeeeeee eeeeeeeee eee ee eeee, eeeeeee (eeeeeeeeeeee eeeeee eeee), eeeeeee, eee eeeeeee eee eeeeeeeee eeeeee (eeeeeeeee, eeeeeeee, eee eeeeeeeeeeeeee) eee eeee eee eeeeeeee eeeeeeee.[‌8‌]

Meeeee 888 Meeeeeeeeeeeeeee ee 8M-Meeeeeeeeeeee[‌888‌]

8-Meeeee- eee 8-eeeee-8M-eeeeeeeeeeeeee 888 (M=Me, Me) eeeeeee eeeeeeeeeeeee eeeeeeee ee eeeeeee ee eeeeee 8- eee 8-(8-eeeeeeeee)eeeeeeeeeeeeee, eeee eeeee eeeeeeeeeeeee, ee eeee eeeeee.[‌888‌,‌888‌] 8-Meeee-8M-eeeeeeeeeeeee ee eeee eeee eeeeeeee eeee eee eeeeee eeeeeeeeee. Mee eeeeeee, eee eeeeeeee ee 888 (M=Me) ee eeeeeeeeeee (eeeeee eeeeeeee 888 eee 888) ee eeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee eeeeeeee eeee e eeeeeeee eeee ee eeeeeeeeeeeee 8 eeeee eee 888 (M=Me), eeeeeee eee eee eeeeeeeeee ee 888 (M=Me) (Meeeee 888). M,8,8,8,8-Meeeeeeeeeeeeeeeeeeeeeee, eeeeeeee eeeeeeeee eeeeeeeee ee eeeeeee eeeeeeee, eeee eeeeeeeee eeeee eeeeeeee ee eeeeeee.[‌888‌] 8-Meeeee-8M-eeeeeeeeeeeee eeee eeeee eeeeeeee eeeeeeee eeee eeeeeeee eee eeee eeeeee.[‌888‌]

Meeeee 888 Meeeeeee ee 8-Meee-8M-eeeeeeeeeeeeee ee Meeeeee[‌888‌,‌888‌]

Mee eeeeeeee ee 8M-eeeeeeeeeeee-8-ee eeeeeeeeeee eeee eeeee eeeeeee ee eee eeeeeeee ee e eeee eeeeeee eeeeee eee 8-eeeeee eeeeeeeeeee 888, eee eee M-eeeee eeeeeeeeeee 888 eee eeee ee eeeeee (Meeeee 888). Mee eeeeeee, eeeeeeeeeee ee 8M-eeeeeeeeeeee-8-ee eeee eeeeeeeeeee, ee eeeeeeee/eeeeee eeeeeeeee, eeeeeee e eeeeeee ee eee M- eee M-eeeeee eeeeeeeeeee.[‌888‌,‌888‌,‌888‌] Meeeeee, eeeee eee eeee eeeeeeeeee, 8-eeeee-8M-eeeeeeeeeeee-8-ee eee 8-eeeee-8M-eeeeeeeeeeee-8-ee eeee eeee eee 8-eeeeeee eeeeeeeee.[‌888‌,‌888‌] Meeeeeee ee 8M-eeeeeeeeeeee-8-ee eeee 8-eeeeeee-8-eeeeeeeeee ee eeeeeeeeeeee, eeee eeeeeeeee eeeeeeeee ee eeee, eeeee eeee eee M-eeeee eeeeeeeeee ee 88% eeeee.[‌888‌] M eeeee ee 8-eeeeee-8,8-eeeeeeee-8M-eeeeeeeeeeeee eeeeeeeeeee ee eeeeeeee ee eeeeeeee ee eee eeeeee eeee ee 8,8-eeeeeeee-8M-eeeeeeeeeeee-8-ee eeee eee eeeeeeeeeee eeeee eeeeeee.[‌888‌] Meeeeee 8-eeeeee-8-eeeee-8M-eeeeeeeeeeeee eeeeeeeeeee eee eeeeeeee ee eeeeeeeeee ee eee 8-eeeeeee eeeeeeeeee eeee eeeee eeeeeee eeeee eeeee-eeeeeeee eeeeeeeeee.[‌888‌]

Meeeee 888 Meeeeeeeee ee 8M-Meeeeeeeeeee-8-eee eeee Meeee Meeeeee[‌888‌‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeee ee 8M-Meeeeeeeeeeee eeee Meeee Meeeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeeee eeeeeeee eeee e MeMe8 eeeee eeee eee eeeeeeee eeeeeee eee eeeeeeeeee eeeeee eeeeee MeMM (88eeee), MMM (888eM), 8M-eeeeeeeeeeeee (88eeee), eee eee eeeee eeeeee (88eeee). Meeee eeeeeeee eee 8888eee, eee eeeeeee eee eeeeee eeee M8M (8888eM) ee eeee e eeeee ee eeee eeeeeee. Meeeee eeee eeeeeeeee ee eeeeeeeeee, eeeeee eeee M8M (88eM), eee eeeee, eeeee eee eeee eeeeeeee eeee eeeeeeeee eeee MMMe8 (8×88eM), eeeeee eeee M8M (8×88eM), eeeee (MeMM8), eee eee eeeeeee eeeeeeeeee eeeee eeeeeee eeeeeeee. 8-Meeee- eee 8-eeeeeeeeeeeeeeeeee eeeeeee eeee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee/MMMe8 8:8).

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