Sodium hydride → 2-(2-Chloro-4-nitro-phenylsulfanyl)-benzothiazole-5-carbonitrile

HRID 1865532Notes

Reaction equation

HRID 1865532 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[N:6]=1.[Cl:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1F.[H-].[Na+]>CN(C=O)C>[Cl:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[S:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 178509540HCID 178509540, compound

Product 1

HCID 221487512-(2-Chloro-4-nitro-phenylsulfanyl)-benzothiazole-5-carbonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared using the method of example 258, starting with 2-mercapto-benzothiazole-5-carbonitrile (243) (960 mg, 5.0 mmol), 2-chloro-1-fluoro-4-nitrobenzene (Aldrich, 878 mg, 5.0 mmol) and NaH (Aldrich, 60% suspension, 200 mg, 5.0 mmol) in DMF (25 mL). Compound 263 (1.60 g, 92%) was obtained as a yellow solid.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-09298b0d459d4410be863aded6db75f6
Source dataset
uspto-grants-2009_12
Patent number
US07626033B2

Reaction notes

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