Thiophosgene → N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamide

HRID 410068Notes

Reaction equation

HRID 410068 reaction equation
[NH2:1][C:2]1[C:3]([Cl:17])=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9].[C:18](Cl)(Cl)=[S:19]>O1CCOCC1.O>[Cl:17][C:3]1[C:2]([N:1]=[C:18]=[S:19])=[C:15]([Cl: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

5

Reactant 2

HCID 10040ThiophosgeneHCID 56839975N-(3-Amino-2,4-dichlorobenzyl)pivalamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-(3-amino-2,4-dichloro-benzyl)-2,2-dimethyl-propionamide (0.95 g, 3.4 mmol) in 4.0 mL dioxane is added to thiophosgene (0.45 mL, 5.8 mmol) in 2.5 mL water. The mixture is stirred overnight, extracted with DCM and the organic phase is washed with 5% aq NaHCO3 solution and water and dried with Na2SO4. After filtration and concentration, the crude product is diluted with DCM, filtered through a pad of silica gel and concentrated.

Workup

  1. extractionextracted with DCM
  2. washthe organic phase is washed with 5% aq NaHCO3 solution and water
  3. dry with materialdried with Na2SO4
  4. filtrationAfter filtration and concentration
  5. additionthe crude product is diluted with DCM
  6. filtrationfiltered through a pad of silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2d4e80afdced4e39b4531ad5c0ce85dc
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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