Water → HCID 18422160, compound

HRID 649965Notes

Reaction equation

Br[C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH2:10]1[C:4]2[C:3]3[C:11](=[O:12])[NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[O:20][C:2]=3[S:6][C:5]=2[CH2:7][CH2:8][CH2:9]1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 2-bromo-4,5,6,7-tetrahydro-N-(2-hydroxyphenyl)-benzo[b]thiophene-3-carboxamide (5.3 g) in dimethyl sulfoxide (50 ml) was added potassium carbonate (4.2 g) and the mixture was stirred at 140° C. for 4 hours. The completion of the reaction was confirmed by thin layer chromatography. The mixture was cooled to room temperature and the reaction mixture was poured into water (300 ml). After neutraliation with hydrochloric acid, the mixture was extracted twice with chloroform and washed with saturated brine. The organic layer was dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give 1,2,3,4-tetrahydro-[1]benzothieno[2,3-b][1,5]benzoxazepin-12(11H)-one (2.1 g).

Workup

temperatureThe mixture was cooled to room temperature
extractionAfter neutraliation with hydrochloric acid, the mixture was extracted twice with chloroform
washwashed with saturated brine
dry with materialThe organic layer was dried over magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record: ord-7f202dbe635b4053a3517e8c5e8d3b3c
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271225B1

Reaction notes

Loading…