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

HRID 2042787Notes

Reaction equation

HRID 2042787 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 fltration 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. concentrationAfter fltration 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-5d56e5e3a6c04c45badfced46eac9fc4
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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