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Phosgene → 10-Methoxy-5H-dibenz(b,f)azepine-5-carbonyl chloride

HRID 41345
Notes
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Reaction equation

HRID 41345 reaction equation
C1C=CC2N(C(N)=O)C3C=CC=CC=3C(=O)CC=2C=1.[CH3:20][O:21][C:22]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[NH:26][C:25]2[CH:33]=[CH:34][CH:35]=[CH:36][C:24]=2[CH:23]=1.[C:37](Cl)([Cl:39])=[O:38]>>[CH3:20][O:21][C:22]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]([C:37]([Cl:39])=[O:38])[C:25]2[CH:33]=[CH:34][CH:35]=[CH:36][C:24]=2[CH:23]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 34312Oxcarbazepine2×HCID 7842410-Methoxyiminostilbene

Product 1

HCID 1605008110-Methoxy-5H-dibenz(b,f)azepine-5-carbonyl chloride

Procedure

U.S. Pat. No. 3,642,775 assigned to Ciba-Geigy Corporation, claims Oxcarbazepine specifically and discloses the process for the preparation of Oxcarbazepine, wherein 10-methoxy-5H-dibenz[b,f]azepine is reacted with phosgene gas to give 10-methoxy-5H-dibenz[b,f]azepine-5-carbonyl chloride and ammonolysis of the resultant compound to give the amide followed by hydrolysis to give Oxcarbazepine.

Sources & evidence

ORD record
ord-60bf5f9e5dc041ce8cc30181f4c613f9
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530647B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes