Thiophosgene → HCID 86632913, compound

HRID 1628560Notes

Reaction equation

HRID 1628560 reaction equation
[C:1](Cl)(Cl)=[S:2].[Cl:5][C:6]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([Cl:15])[C:7]=1[NH2:8]>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:5][C:6]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([Cl:15])[C:7]=1[N:8]=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 124068452,6-Dichloro-4-methoxyaniline

Product 1

HCID 86632913HCID 86632913, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Thiophosgene (1.62 mL, 21.8 mmol) was added dropwise to a stirred mixture of 2,6-dichloro-4-methoxyaniline (2.00 g, 10.4 mmol) in tetrahydrofuran (25 mL) and saturated aqueous sodium hydrogen carbonate (25 mL) at 0° C. The mixture was stirred at room temperature for 1 h, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was washed with n-hexane to give the title compound as a brown solid (2.21 g, 9.44 mmol, 91%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-edbb9b56790348dab0e95f30794d8160
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

Loading…