1,1'-Thiocarbonyldiimidazole → N-(3-Isothiocyanato-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

HRID 1258749Notes

Reaction equation

HRID 1258749 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][C:17]([F:20])([F:19])[F:18])[CH2:5][NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9].C1N=CN([C:26](N2C=NC=C2)=[S:27])C=1>CC#N>[N:1]([C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][C:17]([F:18])([F:19])[F:20])[CH2:5][NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])=[C:26]=[S:27]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 67975180N-(3-Amino-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

Product 1

HCID 86674354N-(3-Isothiocyanato-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(3-amino-4-trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide (200 mg, 0.69 mmol), TCDI (133 mg, 0.746 mmol) and MeCN (3 mL) was refluxed for 1 h. Concentration and purification by column chromatography gave the sub-title compound.

Workup

  1. temperaturewas refluxed for 1 h
  2. concentrationConcentration and purification by column chromatography

Sources & evidence

ORD record
ord-e2acd49c3d0244c697a35e904d473f78
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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