1-Fluoro-2-nitrobenzene → HCID 58015271, compound

HRID 243524Notes

Reaction equation

HRID 243524 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[SH:12])[CH3:2].F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22]>>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[S:12][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])[CH3:2]

Participants

3

Reactant 2

HCID 738951-Fluoro-2-nitrobenzeneHCID 16217758Ethyl 5-fluoro-2-sulfanylbenzoate

Product 1

HCID 58015271HCID 58015271, compound

Procedure

Thus, in a five-step process: 5-fluoro-2-mercapto-benzoic acid ethyl ester may be reacted with 1-fluoro-2-nitrobenzene to form 5-fluoro-2-(2-nitro-phenylsulfanyl)-benzoic acid ethyl ester; the ethyl ester may be converted to 5-fluoro-2-(2-amino-phenylsulfanyl)-benzoic acid ethyl ester; the aminophenyl compound may be cyclized to form 2-fluoro-10H-dibenzo[b,f][1,4]thiazepin-11-one, that may be converted to 11-chloro-2-fluoro-dibenzo[b,f][1,4]thiazepine, and that may be then reacted with piperazine to form the title compound.

Sources & evidence

ORD record
ord-8599a075b47948efbb7999b1c0cbd7b6
Source dataset
uspto-grants-2014_02
Patent number
US08653257B2

Reaction notes

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