Ammonia → HCID 15549909, compound

HRID 840963Notes

Reaction equation

CC1C=CC(S([N:11]2[CH2:17][CH2:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13]3[CH:23]=[CH:24][CH:25]=[CH:26][C:12]2=3)(=O)=O)=CC=1.CS(O)(=O)=O.C1(SC)C=CC=CC=1.N>FC(F)(F)C(O)=O>[NH:11]1[CH2:17][CH2:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

The ethyl 1-(4-methylphenylsulfonyl)-2,3-dihydro-1H-benz[b]azepine-4-carboxylate (0.63 g, 1.70 mmol) synthesized in Reference Example 4 was added to a mixture of trifluoroacetic acid (10 ml), methanesulfonic acid (0.30 g) and thioanisole (1.0 ml) which had been cooled to 0° C., and the resulting mixture was stirred at room temperature for 3.5 hours. The reaction mixture was poured into cooled aqueous ammonia and extracted twice with ethyl acetate, and the extract solution was washed twice with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; ethyl acetate:n-hexane=5:95) to obtain 0.32 g of ethyl 2,3-dihydro-1H-benz [b]azepine-4-carboxylate.

Workup

additionThe reaction mixture was poured
extractionextracted twice with ethyl acetate
washthe extract solution was washed twice with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified by a silica gel column chromatography (eluent; ethyl acetate:n-hexane=5:95)

Sources & evidence

ORD record: ord-e3d538264beb4c3a8f7b33c8507e8e3f
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369110B1

Reaction notes

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