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

HRID 1281872Notes

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-42ef7cb7b22240fd9a4e3c066d5f11df
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455521B1

Reaction notes

Loading…