Water → 7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one

HRID 1886971Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:10][CH2:9][CH2:8][C:7](=[O:22])[C:6]=2[CH:23]=1.S(=O)(=O)(O)O.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][CH2:8][C:7](=[O:22])[C:6]=2[CH:23]=1

Participants

Conditions

Temperature: 25 °C

Procedure

7-Chloro-1-p-toluenesulfonyl-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one (5 g) is added to 90% (w/w) sulfuric acid (50 ml), and the mixture is stirred at 0° C. to 10° C. for 2.5 hours. The reaction mixture is added to a cool water (50 mL) and then is neutralized by gradually adding thereto a solution of sodium hydroxide (75 g) in an appropriate amount of water with attention to exothermal reaction. The reaction mixture is cooled to 25° C., and the resulting yellowish green suspension is extracted with toluene (50 mL), and the organic layer is separated, washed with water (25 ml×2) and dried over sodium sulfate. After filtering off sodium sulfate, the filtrate is concentrated under reduced pressure to give a pale yellow crystals. The crystals are subjected to azeotropic dehydration with toluene in order to remove a slight amount of water to give 7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one having a moisture content of less than 100 ppm (2.5 g, yield 89%, M.p. 103-104° C.).

Workup

additionby gradually adding
extractionthe resulting yellowish green suspension is extracted with toluene (50 mL)
customthe organic layer is separated
washwashed with water (25 ml×2)
dry with materialdried over sodium sulfate
filtrationAfter filtering off sodium sulfate
concentrationthe filtrate is concentrated under reduced pressure
customto give a pale yellow crystals
customto remove a slight amount of water

Sources & evidence

ORD record: ord-ab8529b7d683433d9ddbdb58275697dd
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501730B2

Reaction notes

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