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

HRID 1835537
Notes
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Reaction equation

HRID 1835537 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]=[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]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:5]=2[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 1785095042-Sulfanylidene-2,3-dihydro-1,3-benzothiazole-6-carbonitrile

Product 1

HCID 221488292-(2-Chloro-4-nitro-phenylsulfanyl)-benzothiazole-6-carbonitrileYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

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), 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 261 (1.62 g, 93%) was obtained as a yellow solid.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-77bdeb1f78534158b2f0cfda3f3b0bbe
Source dataset
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06770648B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes