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

HRID 1189614Notes

Reaction equation

HRID 1189614 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-4b8664185ed14cc283ca4b6755b46d9b
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

Loading…