Sodium hydride → 2-(2,6-Dichloro-4-nitro-phenylsulfanyl)-benzothiazole-6-carbonitrile

HRID 1865529Notes

Reaction equation

HRID 1865529 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[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]=[C:16]([Cl:23])[C:15]=1Cl.[H-].[Na+]>CN(C=O)C>[Cl:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:15]=1[S:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 883653,4,5-TrichloronitrobenzeneHCID 1785095042-Sulfanylidene-2,3-dihydro-1,3-benzothiazole-6-carbonitrile

Product 1

HCID 221487332-(2,6-Dichloro-4-nitro-phenylsulfanyl)-benzothiazole-6-carbonitrileYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared using the method of example 258, starting with 2-mercapto-benzothiazole-6-carbonitrile (241) (960 mg, 5.0 mmol), 1,2,3-trichloro-5-nitrobenzene (Acros, 1.13 g, 5.0 mmol) and NaH (Aldrich, 60% suspension, 200 mg, 5.0 mmol) in DMF (25 mL). Compound 260 (1.9 g, 99%) was obtained as a yellow solid.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6f273c773c2543ee942a852da5a9e118
Source dataset
uspto-grants-2009_12
Patent number
US07626033B2

Reaction notes

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