Benzyl Isothiocyanate → HCID 178526718, compound

HRID 1856804Notes

Reaction equation

HRID 1856804 reaction equation
C(N=C=S)C1C=CC=CC=1.C(NC(=S)NN)C1C=CC=CC=1.ClC(O[CH2:27][CH3:28])=O.[CH2:29]([N:36]1[C:40]([SH:41])=[N:39][N:38]=[C:37]1[OH:42])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Br[C:44]1[S:45][C:46]([N+:49]([O-:51])=[O:50])=CN=1>>[CH2:29]([N:36]1[C:40]([S:41][C:44]2[S:45][C:46]([N+:49]([O-:51])=[O:50])=[CH:27][CH:28]=2)=[N:39][N:38]=[C:37]1[OH:42])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 5

HCID 2346Benzyl IsothiocyanateHCID 10928Ethyl chloroformateHCID 182112-Bromo-5-nitrothiazoleHCID 7371353-Amino-1-benzylthioureaHCID 178518950HCID 178518950, compound

Product 1

HCID 178526718HCID 178526718, compoundYield 17.9%

Procedure

The title compound was prepared in a manner similar to that described in Example 5 starting with benzyl isothiocyanate. The intermediate 4-benzyl-3-thiosemicarbazide (1.81 g) was treated with ethyl chloroformate (1.09 g) as in Example 5. The reaction product 4-benzyl-3-hydroxy-5-mercapto-1,2,4-triazole (1.04 g) was reacted with 1.05 g of 2-bromo-5-nitrothiazole as in Example 5. Crystallization from ethanol and water gave 0.3 g of 4-benzyl-3-hydroxy-5-[(5-nitrothien-2-yl)mercapto]1,2,4-triazole, a yellow solid, MP 221-224° C.

Workup

  1. customThe title compound was prepared in a manner similar to
  2. customCrystallization from ethanol and water

Sources & evidence

ORD record
ord-69fc8a55d3a843c9b4fcfdf2b056322c
Source dataset
uspto-grants-2000_11
Patent number
US06143765

Reaction notes

Loading…