Potassium Carbonate → HCID 10879383, compound
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[CH:16]=[CH:15][S:14][C:13]=1Br)=[O:11].[C:18](=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:18][C:15]1[S:14][C:13]2[O:1][C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=3[NH:9][C:10](=[O:11])[C:12]=2[CH:16]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 145 °C
Procedure
To a solution of N-(2-hydroxy-5-methylphenyl)-2-bromo-3-thiophenecarboxamide (2.9 g) in dimethyl sulfoxide (24 ml) was added potassium carbonate (2.4 g) and the mixture was stirred at 140-150° C. for 2 hours. The reaction system was cooled to room temperature and the reaction mixture was poured into ice water. The precipitated crystals were collected by filtration. The filtrate was extracted twice with chloroform and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue and the above-mentioned crystals were combined and purified by silica gel column chromatography (chloroform:methanol=20:1). The obtained solid was collected by filtration from hexane to give 2,7-dimethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.0 g).
Workup
- temperatureThe reaction system was cooled to room temperature
- filtrationThe precipitated crystals were collected by filtration
- extractionThe filtrate was extracted twice with chloroform
- dry with materialthe organic layer was dried over sodium sulfate
- customThe solvent was evaporated under reduced pressure
- custompurified by silica gel column chromatography (chloroform:methanol=20:1)
- filtrationThe obtained solid was collected by filtration from hexane
Sources & evidence
- ORD record
- ord-f1a211d4811b46ce9a845a8bddac985a
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455521B1
Reaction notes
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