Hydrochloric Acid → 7-Chloro-1,2,3,4-tetrahydro-1-[(4-methylphenyl)sulfonyl]-5H-1-benzazepin-5-one

HRID 570902Notes

Reaction equation

HRID 570902 reaction equation
ClC1C=CC2NCCCC(=O)C=2C=1.ClC1C=CC2N(C(=O)C3C=CC([N+]([O-])=O)=CC=3C)CCCC(=O)C=2C=1.ClC1C=CC2N(C(=O)C3C=CC(NC(=O)C4C=CC=CC=4C)=CC=3C)CCCC(=O)C=2C=1.[Cl:71][C:72]1[CH:73]=[CH:74][C:75]2[N:81]([S:82]([C:85]3[CH:90]=[CH:89][C:88]([CH3:91])=[CH:87][CH:86]=3)(=[O:84])=[O:83])[CH2:80][CH2:79][CH:78](C(OCC)=O)[C:77](=[O:97])[C:76]=2[CH:98]=1.Cl>O.C(O)(=O)C>[Cl:71][C:72]1[CH:73]=[CH:74][C:75]2[N:81]([S:82]([C:85]3[CH:90]=[CH:89][C:88]([CH3:91])=[CH:87][CH:86]=3)(=[O:83])=[O:84])[CH2:80][CH2:79][CH2:78][C:77](=[O:97])[C:76]=2[CH:98]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 113628435-Dehydro TolvaptanHCID 196080657-Chloro-1-(2-methyl-4-nitrobenzoyl)-1,2,3,4-tetrahydro-5H-1-benzazepin-5-oneHCID 229034837-Chloro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one2×HCID 66981125Ethyl 7-Chloro-5-oxo-1-toxyl-2,3,4,5,-tetrahydro-1H-benzo[b]azepine-4-carboxylate

Product 1

HCID 665537647-Chloro-1,2,3,4-tetrahydro-1-[(4-methylphenyl)sulfonyl]-5H-1-benzazepin-5-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Processes for the preparation of 7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one, 7-chloro-1-(2-methyl-4-nitrobenzoyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine and 7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine were reported in Bioorganic & medicinal chemistry 7 (1999), 1743-1754. According to the journal, 7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one can be prepared by reacting 7-chloro-4-ethoxycarbonyl-5-oxo-N-p-toluenesufonyl-2,3,4,5-tetrahydro-1H-1-benzazepine with acetic acid in the presence of hydrochloric acid and water to obtain 7-chloro-5-oxo-2,3,4,5-tetrahydro-1-p-toluenesulfonyl-1H-1-benzazepine, and then reacted with polyphospholic acid.

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-ea693a92fa504510ab6c1b2ca232092c
Source dataset
uspto-grants-2015_05
Patent number
US09024015B2

Reaction notes

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