Hydrochloric Acid → HCID 14722442, compound
Reaction equation
Br[C:2]1[O:3][C:4]2[CH:15]=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:13]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:12][C:5]=2[C:6](=[O:11])[C:7]=1[NH:8][CH:9]=[O:10].O.Cl.[CH3:30][N:31](C)C=O>>[C:30]([C:2]1[O:3][C:4]2[CH:15]=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:13]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:12][C:5]=2[C:6](=[O:11])[C:7]=1[NH:8][CH:9]=[O:10])#[N:31]Participants
Procedure
4.25 g of 2-bromo-3-formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one was dissolved in 50 ml of N,N-dimethylformamide. 1.97 g of cuprous cyanide was added thereto, and the resulting mixture was stirred for 2 hours at 85°-90° C. The reaction mixture was introduced into 300 ml of water, adjusted to pH 4 with 4N hydrochloric acid, and extracted with two 200-ml portions of ethyl acetate. The extracts (the organic layers) were combined, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The resulting residue was recrystallized from acetonitrile to obtain 2.05 g (yield: 55.3%) of 2-cyano-3-formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 229°-230° C.
Workup
- extractionextracted with two 200-ml portions of ethyl acetate
- washwashed with water
- dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous sodium sulfate
- customThe solvent was removed by distillation under reduced pressure
- customThe resulting residue was recrystallized from acetonitrile
Sources & evidence
- ORD record
- ord-82782c54291a49ee82289cc230f57d06
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04954518
Reaction notes
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