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

HRID 1189618Notes

Reaction equation

HRID 1189618 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-41dd4c49d35645eeb2b222c2a66d157a
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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