Hydrochloric Acid → 1-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

HRID 2353982Notes

Reaction equation

[NH:1]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.Cl>N1C=CC=CC=1>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([N:1]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]3[CH:9]=[CH:10][CH:11]=[CH:12][C:2]2=3)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1,2,3,4-Tetrahydro-benzo[b]azepin-5-one (500 mg, 3.1 mmol) in pyridine (2 ml) is added p-toluenesulfonyl chloride (650 mg, 3.4 mmol), and the mixture is heated at 50° C. for 1 hour. The reaction mixture is poured into 1N HCl (100 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated to a solid. The solid is purified by silica gel column chromatography (eluent, 30% ethyl acetate in hexanes) to give the title compound as a solid. Mass spectrum (ES+): 316 (M+H).

Workup

extractionextracted with ethyl acetate (3×20 ml)
washThe combined organic extracts are washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated to a solid
customThe solid is purified by silica gel column chromatography (eluent, 30% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-f06cba394b9044918e8c8e1475e4fdf5
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749992B2

Reaction notes

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