1,1'-Thiocarbonyldi-2(1H)-pyridone → N-(2,4-Difluoro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide

HRID 410072Notes

Reaction equation

HRID 410072 reaction equation
[NH2:1][C:2]1[C:3]([F:17])=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9].[C:18](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:19]>O1CCOCC1>[F:17][C:3]1[C:2]([N:1]=[C:18]=[S:19])=[C:15]([F:16])[CH:14]=[CH:13][C:4]=1[CH2:5][NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 56839977N-(3-amino-2,4-difluoro-benzyl)-2,2-dimethyl-propionamide

Product 1

HCID 56840193N-(2,4-Difluoro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-(3-amino-2,4-difluoro-benzyl)-2,2-dimethyl-propionamide (570 mg, 2.35 mmol), 1,1′-thiocarbonyldi-2(1H)-pyridone (550 mg, 2.35 mmol) and dioxane (20 mL) is stirred at reflux overnight. The reaction mixture is concentrated, diluted with DCM, filtered through a pad of silica gel and the filtrate is concentrated to give the title compound.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture is concentrated
  3. additiondiluted with DCM
  4. filtrationfiltered through a pad of silica gel
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-7cb7203615884466bd9db4a34c53b5ee
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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