4-Fluorophenyl isothiocyanate → 1-(5-Chloro-2-(methylthio)pyrimidine-6-carbonyl)-4-(4-fluorophenyl)thiosemicarbazide

HRID 507641Notes

Reaction equation

HRID 507641 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([NH:12][NH2:13])=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[S:23])=[CH:17][CH:16]=1>CCO>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([S:8][CH3:9])=[N:4][C:3]=1[C:10]([NH:12][NH:13][C:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=1)=[S:23])=[O:11]

Participants

4

Reactant 2

HCID 152414-Fluorophenyl isothiocyanateHCID 432447685-Chloro-2-(methylthio)pyrimidine-4-carbohydrazide

Product 1

HCID 602045491-(5-Chloro-2-(methylthio)pyrimidine-6-carbonyl)-4-(4-fluorophenyl)thiosemicarbazideYield 95.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-2-(methylthio)pyrimidine-4-carbohydrazide (8.28 g, 38.0 mmol) and 4-fluoro-phenyl isothiocyanate (5.811 g, 38.0) were added to a 1 liter flask. A minimal amount of EtOH was added, just to ensure proper mixing. This suspension was stirred at room temperature overnight. The EtOH was removed under vacuum to give 13.5 g (95% yield) of product as a light yellow solid. MS (M+H)+ 372.

Workup

  1. customThe EtOH was removed under vacuum

Sources & evidence

ORD record
ord-5822cda951114fa99c69e04bd40b6432
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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