Water → Methyl 7-bromo-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587023Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.N1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[S:23]1C=CC=C1Cl.[OH2:29]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:18]([C:19]3[S:23][CH:22]=[CH:21][CH:20]=3)=[O:29])[CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1

Participants

Conditions

Temperature: 78 °C

Procedure

To a solution of methyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (200 mg) and pyridine (123 mg) in tetrahydrofuran (10 ml) was added 2-thienyl chloride (208 mg) at 0° C., and the mixture was heated at 78° C. overnight. After allowing to cool, to the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. The solvent was evaporated, which was recrystallized from hexane-ethyl acetate to give methyl 7-bromo-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylate (236 mg) as colorless crystals.

Workup

temperatureto cool, to the mixture
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried with magnesium sulfate
customThe solvent was evaporated
customwhich was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record: ord-1ffd5f06a8b64fbd800d5841614c67fb
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936602B1

Reaction notes

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