Ethyl chloroformate → HCID 178526849, compound

HRID 1422011Notes

Reaction equation

HRID 1422011 reaction equation
C1([C:7]([NH:9][C:10](=[S:13])[NH:11][NH2:12])=[O:8])CCCCC1.ClC(O[CH2:18][CH3:19])=O.[CH:20]1(N2C=NN=C2)[CH2:25]CC[CH2:22][CH2:21]1.Br[C:32]1[S:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][N:36]=1>>[OH:8][C:7]1[N:9]([CH:19]2[CH2:18][CH2:22][CH2:21][CH2:20][CH2:25]2)[C:10]([S:13][C:32]2[S:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][N:36]=2)=[N:11][N:12]=1

Participants

5

Reactant 4

HCID 10928Ethyl chloroformateHCID 182112-Bromo-5-nitrothiazoleHCID 22132829HCID 22132829, compoundHCID 53840200HCID 53840200, compound

Product 1

HCID 178526849HCID 178526849, compoundYield 18.2%

Procedure

The title compound was prepared in a manner similar to that described in Example 5. Cyclohexyl isothiocyanate (3.53 g) in 10 mL of acetonitrile was added to hydrazine (0.8 g) in mL of acetonitrile over a period of minutes. The reaction was stirred for two additional hours and evaporated to dryness to give 4.4 g of 4-cyclohexylcarbonyl-3-thiosemicarbazide. 4-Cyclohexylcarbonyl-3-thiosemicarbazide (2.02 g) was treated as in example 5 with ethyl chloroformate (1.08 g). The reaction product 3-hydroxy-5-mercapto]-4-cyclohexyl-1,2,4-triazole (1.0 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 3-hydroxy-5-[(5-nitrothiazol-2-yl)mercapto]-4-cyclohexyl-1,2,4-triazole, a yellow solid, MP 237-239° C.

Workup

  1. customCrystallization from ethanol and water

Sources & evidence

ORD record
ord-495ba323441a470f903211ce7aac7501
Source dataset
uspto-grants-2000_06
Patent number
US06080772

Reaction notes

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