1,1'-Thiocarbonyldi-2(1H)-pyridone → N-(2,4-Dichloro-3-isothiocyanato-benzyl)-2-methyl-2-fluoro-propionamide

HRID 1189626Notes

Reaction equation

HRID 1189626 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])([F:26])[CH3:25]>O.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]([CH3:25])([F:26])[CH3:27]

Participants

5

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 67957110N-(3-Amino-2,4-dichloro-benzyl)-2-methyl-2-fluoro-propionamide

Product 1

HCID 86666461N-(2,4-Dichloro-3-isothiocyanato-benzyl)-2-methyl-2-fluoro-propionamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

1,1′-Thiocarbonyldi-2-pyridone (1.21 g, 5.2 mmol) is added to a mixture of N-(3-amino-2,4-dichloro-benzyl)-2-methyl-2-fluoro-propionamide (1.32 g, 4.7 mmol) and dioxane (25 mL) and it is stirred at reflux for 2 d. The mixture is diluted with water, most of the dioxane is removed under reduced pressure and the resulting precipitate is collected by filtration, washed with water and dried.

Workup

  1. temperatureat reflux for 2 d
  2. customis removed under reduced pressure
  3. filtrationthe resulting precipitate is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-201a2d394466413fafc6c04f8b76c7db
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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