Thiophosgene → HCID 86632895, compound

HRID 1398919Notes

Reaction equation

HRID 1398919 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-42f8d02b49f7472094e3a266985681ac
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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