You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via18.10.8.1.6 Method 6: From Thiocarbonyl Transfer Reagents
Please login to access the full content or check if you have access via
Sato, S.; Furukawa, N., Science of Synthesis, (2005) 18, 905.
Reactions of primary or secondary amines with thiophosgene or isothiocyanates are used widely as a synthetic method for the synthesis of thiourea derivatives. However, these methods are hazardous due to the toxic properties of both thiophosgene and isothiocyanates. Despite their toxicity, these reagents continue to be widely used due to the importance of symmetrical and unsymmetrical thioureas. On the other hand, preparative methods involving the use of thiocarbonyl transfer reagents are more efficient and safer.
Meeeeeeeeeee eeeeeeee eeeeeeee eeee eeeee eeeeeee eeeeeeeee eeeeeeeeeeee ee eee eeeeeeeee ee eee eeeeeeeee. 8,8′-Meeeeeeeeeeeeeeeeeeeeee (888) (eee Meeeeee 88.88.8.8.8) eeeeeeeee eeeeee eeee 8 eeeee eeeeeeeeeee ee ee eeeeeeeee ee eeeeeeee eeeeeee eeeee, eeeeeee 8,8-eeeeeeeeeeeee eeeeeeeee 888. Mee eeeeeeeeeeeee eeeeeeee eeee 8 eeeee eeeeeeeeee ee eeeeeee eeeee eeeeeee ee eee eeeeeeeee ee ee eeeeeeeeeeeeee, eee ee eeeeeeeeeeee ee eee eeeeeeee M-eeeeeeeeeeeeee-8-eeeeeeeeeeeeee 888. Meee e 8 eeeeeeeeee ee e eeeeeeeee eeeee, eee M,M-eeeeeeeeeeeee eeeeeeeee-8-eeeeeeeeeeeeee 888 ee eeeeee (Meeeee 888).[888,888–888]
Meeeee 888 Meeeeeee ee 8,8′-Meeeeeeeeeeeeeeeeeeeeee eeee Meeeee[888,888–888]
Meeeeeeeeee, 8,8′-eeeeeeeeeeeeee(8,8,8-eeeeeeee) (888) eeeeee eeeeeeeeeeeeeee eeee 8 eeeee eeeeeeeeee ee eeeee ee eeeeeee eee M-eeeee-8,8,8-eeeeeeee-8-eeeeeeeeeeeeee (e.e., 888). Mee eeeeeeee eee eeee eeeeeee eee eeee eeee eeeeeeeee eee eeeeeeee eeeeee. Me eeee eeee 8 eeeeeeeeee ee eeeee ee eeeee ee eee eeeeeeee, 8,8-eeeeeeeeeeeee eeeeeeeee (e.e., 888) eee eeeeee (Meeeee 888). Meee ee eeeeeeeeeeee ee ee ee eeeeeeee ee eeeeeee eeeeeeeeeeeeeee eeeeeeeeeee eeeeeeeee eeeeeeee.[888]
M eeeeeeeeeeee eeeeee eeeeeeeeeee ee eeeeeeee eeeeeeeeeee 888 eeeee eeeeeeeee ee eee ee eeee eeeeeeeee ee 8,8′-eeeeeeeeeeeeeeeeeeeeeee (888) eeee 8M-eeeeeeeee, eeeeee eeeeeeeee, eee e 8-eeeeeeeeeeeeee eeee, eeee eeeeeeee eee eee ee eeeeeeeeeeee. Mee eeeeeee ee eeee ee eeee eeeeeeeee 8,8′-eeeeeeeeeeeeeeeeeeeeeee (888) ee eeeeeeeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeeeee eeeeeeeee 888 ee eeeeeeee eeeeeeee ee eee eeeeeeeee eeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeeeee ee ee Meeeeeeeeeeee Meeeeeee Meeee 8,8′-Meeeeeeeeeeeeeeeeeeeeee[888]
Meeeee 8M-eeeeeeeee-8-eeeeeeeeeeeeee (888) eee eee M-eeeeee eeee 888 eee eee eeeeee eeeeeeeeeeee eeeeeeee eeeeeeee eee eeeeeeeee ee eeeeeeeeeee eeeeeeeee 888 (Meeeee 888). Meeee eeeeeeee eee ee eeee eee eee eeeeeeeee ee eeeeeeeeeee eee eeeeeeeeeeeee eeee-, ee-, eee eeeeeeeeeeeeee eeeeeeeee 888 ee eeee eeeeee eeeee eeee eee eeeeee eeeeeeeeeeee eeeeeeee eeeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeeeeeeee Meeeeeeeeeeee Meeeeeeee[888]
M8 | Meeee (%) | Mee | |
---|---|---|---|
Meee 888 | Meee 888 | ||
e-Me | 88 | 88 | [888] |
MM8MM=MM8 | 88 | 88 | [888] |
(MM8)88Me | 88 | 88 | [888] |
Me | 88 | 88 | [888] |
(MM8)8Me | 88 | 88 | [888] |
Me | 88 | 88 | [888] |
Me | 88 | 88 | [888] |
8-MeMM8M8(MM8)8 | 88 | 88 | [888] |
8-eeeeeee | 88 | 88 | [888] |
eeeeeeeeeee | 88 | 88 | [888] |
Meeeee 888 Meeeeeeeeeeee Me- eee Meeeeeeeeeeeee Meeeeeeee[888]
M8 | M8 | M8 | Meeee (%) | Mee | |
---|---|---|---|---|---|
Meee 888 | Meee 888 | ||||
Me | Me | M | 88 | 88 | [888] |
Me | (MM8)8Me | M | 88 | 88 | [888] |
Me | 8-MeMM8M8 | M | 88 | 88 | [888] |
Me | 8-eeeeeee | M | 88 | 88 | [888] |
Me | Me | M | 88 | 88 | [888] |
Me | Me | M | 88 | 88 | [888] |
Me | Me | M | 88 | 88 | [888] |
Me | Me | Me | 88 | 88 | [888] |
Me | (MM8)8 | 88 | 88 | [888] | |
Me | (MM8)8M(MM8)8 | 88 | 88 | [888] | |
Me | M | M | 88 | 88 | [888] |
Me | M | M | 88 | 88 | [888] |
M | Me | Me | 88 | 88 | [888] |
M | (MM8)8 | 88 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
M-Meeeee-8M-8,8,8-eeeeeeee-8-eeeeeeeeeeeeee (888):[888]
Me e eeee ee 8,8′-eeeeeeeeeeeeee(8,8,8-eeeeeeee) (888; 888 ee, 8.88 eeee) ee eeeeeee (88 eM) eee eeeee eeeeeee (888 ee, 8.88 eeee). Mee eeeeee eeeee ee eee eeee eeeeeeeeeee eeeeeeeeeee. Meeeeeee ee M8M eee eeeeeeeeee eeeeeee eeeeeeee e eeeeeeee eeeeee eeeeeeeeeee eeeee eee eeeeeeeee ee eeeeeeeeee ee eeee eeeeeeee; eeeee: 888 ee (88%); ee 88–88°M. Meeeeeeeeeeeeeeee [eeeeeee (MMMMMMM: eeeeeeeeee)/eeeeee] eee eee eeeeeeee eee eeeeeee eeeee.
8,8-Meeeeeeeeeeeeeee (888):[888]
Me e eeee ee 8,8′-eeeeeeeeeeeeee(8,8,8-eeeeeeee) (888; 888 ee, 8.8 eeee) ee MM8Me8 (88 eM) eee eeeee eeeeeee (888 ee, 8 eeee). Mee eeeeee eeeee ee eee eeee eeeeeeeeeee, eee ee eee eeee eeee e eeeeeeeeeee eeeeee. Meeeeeeeee eee eeeeeeeeeeeee ee eee eeeeeee eee eeeeeeeeeeeeeeeee (MeMM/M8M) eeee eee eeeeeee; eeeee: 888 ee (88%); ee 888–888°M.
8-Meeeee-8-eeeeeeeeeeeeee (888, M8 = Me; M8 = Me; M8 = M8 = M); Meeeeee Meeeeeeee:[888]
M-Meeeee-M-eeeeee-8M-eeeeeeeee-8-eeeeeeeeeeeeee:
MMMMMMM: Meeeee eeeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee ee eeeeeeeeee, eeee eeeeeeeeee, eee eeeeeeeee.
MeM (888 ee) eee eeeeee eeee eeeeee eee eeee eeeeeeeee ee MMM (8 eM), eee eee eeeeeee eee eeeeee ee 8°M. Me eeee eee eeeee 8M-eeeeeeeee (888 ee, 8.88 eeee) eee MM8 (8.8 eM) eeeeeeee ee eeeeeeee eee 88 eee ee 8°M. Meee, 8-eeeeeeeeeeeeee eeee (8.88 eeee) eee eeeee eee eee eeeeee eeeeeee eee eeeeeee ee ee eee 8 e. M-Meeeeeeeeeeeeeeee (8.88 eM) eee eeeee eee eee eeeeeee eee eeeeeee eee 8 e. Mee eeeeeee eee eeeeeee ee eeeee, eee eeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeeeeee (MeMMe) eeee eee eeeeeee ee ee eee; eeeee: 888 ee (88%). Meee eee eee eeee eee eeeeeeeeee eeeeeeee eeeeeee eeeeeee eeeeeeeeeeee.
8-Meeeee-8-eeeeeeeeeeeeee (888, M8 = Me; M8 = Me; M8 = M8 = M):
M eeeeeee ee M-eeeeee-M-eeeeee-8M-eeeeeeeee-8-eeeeeeeeeeeeee (888 ee, 8.88 eeee) ee 88% MM8 ee MeMM (8 eM) eee eeeeeee eeeeeeeee ee ee. Mee eeeeeee eee eeeeeee ee eeeee eee eee eeeeeee eeeeeeeeeeeeeee (MeMMe) ee eeee M-eeeeee eeeeee(eeeeee)eeeeeeeeeeeee ee ee eee; eeeee: 88 ee (88%) eee 888 (M8 = Me; M8 = Me; M8 = M8 = M); eeeee: 88 ee (88%); ee 888–888°M.
References
[124] | Meeeee, M.; Meeeeee, M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[456] | eee Meeee, M. M.; Meeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 88. |
[457] | eee Meeee, M. M.; Meeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
[458] | Meeeeeee, M. M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[459] | Meeeeee, M.; Meeeee, M.; Meeeeee, M. M., Meee Meee. Meeee., (8888) 88, 8888. |
[460] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[461] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeee, M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[462] | Meeeeeee, M.; Meeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[463] | Meeeeee, M. M.; Meee, M.; Meeee, M. M.; Mee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.