Potassium Carbonate → 8-methoxy-2-methylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

HRID 649997Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]([C:13]1[CH:17]=[C:16]([CH3:18])[S:15][C:14]=1Br)=[O:12].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[NH:10][C:11](=[O:12])[C:13]3[CH:17]=[C:16]([CH3:18])[S:15][C:14]=3[O:1][C:2]=2[CH:7]=1

Participants

Conditions

Temperature: 145 °C

Procedure

To a solution of N-(2-hydroxy-4-methoxyphenyl)-2-bromo-5-methyl-3-thiophenecarboxamide (2.1 g) in dimethyl sulfoxide (17 ml) was added potassium carbonate (1.7 g), and the mixture was stirred at 145° 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 and the obtained crystals were purified by silica gel column chromatography (chloroform:methanol=20:0-20:1). The obtained solid was collected by filtration from diisopropyl ether-ethyl acetate—methanol to give 8-methoxy-2-methylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (530 mg).

Workup

temperatureThe reaction system was cooled to room temperature
filtrationThe precipitated crystals were collected by filtration
customthe obtained crystals were purified by silica gel column chromatography (chloroform:methanol=20:0-20:1)
filtrationThe obtained solid was collected by filtration from diisopropyl ether-ethyl acetate—methanol

Sources & evidence

ORD record: ord-d1dba8c6603647c0938803fdf43daf47
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271225B1

Reaction notes

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