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

HRID 1258696Notes

Reaction equation

HRID 1258696 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[NH2:17][C:18]1[C:19]([F:33])=[C:20]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:21][NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25]>O1CCOCC1>[F:33][C:19]1[C:18]([N:17]=[C:1]=[S:2])=[C:31]([F:32])[CH:30]=[CH:29][C:20]=1[CH2:21][NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25]

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

1,1′-Thiocarbonyldi-2-pyridone (546 mg, 2.35 mmol) was added to a mixture of N-(3-amino-2,4-difluoro-benzyl)-2,2-dimethyl-propionamide (570 mg, 2.35 mmol) and dioxane (20 mL) and stirred at reflux overnight. The mixture was concentrated, diluted with DCM and filtered over silica gel. The filtrate was concentrated to give the sub-title compound.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with DCM
  4. filtrationfiltered over silica gel
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-83a84f38d0a942d9ad640438519713a2
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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