Thiophosgene → HCID 86632895, compound

HRID 1628562Notes

Reaction equation

HRID 1628562 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][C:7]=1[CH3:15]>O1CCCC1.C(=O)([O-])O.[Na+]>[N:5]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][C:7]=1[CH3:15])=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 121180574-amino-3-methylbenzamide

Product 1

HCID 86632895HCID 86632895, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Thiophosgene (2.57 mL, 34.6 mmol) was added dropwise to a stirred mixture of 4-amino-3-methylbenzamide (2.60 g, 17.3 mmol) in tetrahydrofuran (43 mL) and saturated aqueous sodium hydrogen carbonate (43 mL) at 0° C. The mixture was stirred at room temperature for 10 min, 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 diisopropylether to give the title compound as a brown solid (3.02 g, 15.7 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 diisopropylether

Sources & evidence

ORD record
ord-044b47c6e852492d97180bb972a58544
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

Loading…