1,1'-Thiocarbonyldiimidazole → N-(4-Chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

HRID 1410213Notes

Reaction equation

HRID 1410213 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][NH:6][C:7]([C:9]1([C:12]([F:15])([F:14])[F:13])[CH2:11][CH2:10]1)=[O:8].C1N=CN([C:25](N2C=NC=C2)=[S:26])C=1>C(Cl)Cl>[Cl:19][C:18]1[CH:17]=[CH:16][C:4]([CH2:5][NH:6][C:7]([C:9]2([C:12]([F:13])([F:14])[F:15])[CH2:10][CH2:11]2)=[O:8])=[CH:3][C:2]=1[N:1]=[C:25]=[S:26]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 59529866N-(3-amino-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Product 1

HCID 86646336N-(4-Chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(3-amino-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide (5.21 g; 17.79 mmol) in DCM (40 mL) was added to a solution of TCDI (3.80 g; 21.34 mmol) in DCM (30 mL) at 0° C. After 12 h at rt, the mixture was concentrated and the residue was purified by column chromatography to give the sub-title compound. Yield: 5.00 g (84%).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4f47b4f1957642a990fc6f3d70946c34
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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