Stannous Chloride → HCID 10265481, compound

HRID 1824586Notes

Reaction equation

HRID 1824586 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[N+:19]([O-])=O)[CH3:3].Cl[Sn]Cl>>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH2:19])[CH3:1]

Participants

3

Reactant 2

HCID 24479Stannous ChlorideHCID 11415526HCID 11415526, compound

Product 1

HCID 10265481HCID 10265481, compound

Procedure

The authentic sample, N,N-dimethyl-2-(2-amino-4-fluorophenylthio)benzylamine (12) vas also synthesized in multisteps. Reaction of 2-chloro-5-fluoronitrobenzene with 2-thio-N,N-dimethylbenzamide gave N,N-dimethyl-2-(2-nitro-4-fluorophenylthio)-benzamide (9). Reduction of compound 9 with BH3 gave N,N-dimethyl-2-(2-nitro-4-fluorophenylthio)benzylamine (10) and its amine borane (11) in a ratio of ˜1:1 (Scheme 1). Compound 10 was reduced further with SnCl2 to give the final product (12).

Sources & evidence

ORD record
ord-f0eaf12d947348269c75096882d2a27e
Source dataset
uspto-grants-2006_05
Patent number
US07041851B2

Reaction notes

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