Sulfuric Acid → 4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one

HRID 726700Notes

Reaction equation

[F:1][C:2]1([F:24])[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:4][CH2:3]1.S(=O)(=O)(O)O.[OH-].[K+]>C(O)(=O)C>[F:24][C:2]1([F:1])[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

4,4-Difluoro-1-tosyl-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one (3.00 g) was dissolved in 14 ml of acetic acid, 7 ml of concentrated sulfuric acid was added to the solution and then the resulting mixture was heated at 60° C. for 10 hours. The reaction solution was ice-cooled, adjusted to a basic range with potassium hydroxide and extracted three times with ethyl acetate, and the resulting organic layer was dried over anhydrous potassium carbonate. By evaporating the reaction solvent, 4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one was obtained. This product was used in the following reaction without purification.

Workup

temperaturecooled
extractionextracted three times with ethyl acetate
dry with materialthe resulting organic layer was dried over anhydrous potassium carbonate
customBy evaporating the reaction solvent

Sources & evidence

ORD record: ord-a42f7444b4884a8fa6be32f8538a896b
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05710150

Reaction notes

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