1,1'-Thiocarbonyldi-2(1H)-pyridone → N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamide

HRID 410064Notes

Reaction equation

HRID 410064 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[NH2:17][C:18]1[C:19]([Cl:33])=[C:20]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:21][NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25]>O1CCOCC1>[Cl:33][C:19]1[C:18]([N:17]=[C:1]=[S:2])=[C:31]([Cl: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 56839975N-(3-Amino-2,4-dichlorobenzyl)pivalamide

Product 1

HCID 56840192N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1′-Thiocarbonyldi-2-pyridone (4.87 g, 21 mmol) is added to a mixture of N-(3-amino-2,4-dichloro-benzyl)-2,2-dimethyl-propionamide (5.50 g, 20 mmol) and dioxane (200 mL) and stirred at rt for 2 h and at reflux for 8 h. The mixture is concentrated, diluted with DCM and filtered over silica gel. The filtrate is concentrated to give the sub-title compound.

Workup

  1. temperatureat reflux for 8 h
  2. concentrationThe mixture is concentrated
  3. additiondiluted with DCM
  4. filtrationfiltered over silica gel
  5. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-f0e14495c2b44bbeabd7764e21dff872
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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