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

HRID 2042791Notes

Reaction equation

HRID 2042791 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-74eaeb37beaf44d0841e0c85c34ee7ae
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

Loading…