2-(2-Chloro-4-nitro-phenylsulfanyl)-benzothiazole-5-carbonitrile → 2-(4-Amino2-chlorophenylsulfanyl)-benzothiazole-5-carbonitrile

HRID 1835546Notes

Reaction equation

HRID 1835546 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[S:11][C:12]1[S:13][C:14]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:15]=2[N:16]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([S:11][C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:15]=3[N:16]=2)=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 2

HCID 221487512-(2-Chloro-4-nitro-phenylsulfanyl)-benzothiazole-5-carbonitrileHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 221489052-(4-Amino2-chlorophenylsulfanyl)-benzothiazole-5-carbonitrileYield 93%

Procedure

The title compound was prepared using the method of example 270, starting with 2-(2-chloro-4-nitro-phenylsulfanyl)-benzothiazole-5-carbonitrile (263) (1.59 g, 4.58 mmol), tin chloride dihydrate (Aldrich, 5.18 g, 22.9 mmol). Compound 275 (1.35 g, 93%) was obtained as a yellowish solid.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0a1b5f12fb6444faa0e01f08df0cd66a
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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