2-(2,6-Dichloro-4-nitro-phenylsulfanyl)-benzothiazole-5-carbonitrile → 2-(4-Amino-2,6-dichlorophenylsulfanyl)-benzothiazole-5-carbonitrile

HRID 1835545Notes

Reaction equation

HRID 1835545 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[S:12][C:13]1[S:14][C:15]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][C:16]=2[N:17]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([S:12][C:13]2[S:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][C:16]=3[N:17]=2)=[C:4]([Cl:11])[CH:5]=1

Participants

3

Reactant 2

HCID 221487682-(2,6-Dichloro-4-nitro-phenylsulfanyl)-benzothiazole-5-carbonitrileHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 221488262-(4-Amino-2,6-dichlorophenylsulfanyl)-benzothiazole-5-carbonitrileYield 80%

Procedure

The title compound was prepared using the method of example 270, starting with 2-(2,6-dichloro-4-nitro-phenylsulfanyl)-benzothiazole-5-carbonitrile (262) (1.9 g, 4.97 mmol), tin chloride dihydrate (Aldrich, 5.62 g, 24.9 mmol). Compound 274 (1.40 g, 80%) was obtained as a yellowish solid.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-3ede3310f7ce4e1b84fab031652bbfe6
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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