2,5-Dichloronitrobenzene → 2-(4-Chloro-2-nitro-phenylamino)-thiophene-3-carbonitrile

HRID 131378

Reaction equation

HRID 131378 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]#[N:19].O.[OH-].[Li+]>CS(C)=O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:12][C:13]2[S:14][CH:15]=[CH:16][C:17]=2[C:18]#[N:19])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 69772,5-DichloronitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 7366072-Aminothiophene-3-carbonitrile

Product 1

HCID 692103022-(4-Chloro-2-nitro-phenylamino)-thiophene-3-carbonitrileYield 86.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine 1,4-dichloro-2-nitro-benzene (3.87 g, 20.13 mmol), 2-aminothiophene-3-carbonitrile (2.50 g, 20.13 mmol), and DMSO (25.0 ml). Add lithium hydroxide monohydrate (1.69 g, 40.27 mmol) all at once and then stir the mixture at ambient temperature for 24 hours. Pour the mixture onto ice chips and stir it for 1.5 hours. Remove the resulting orange precipitate by vacuum filtration and then dry it under vacuum to give 4.85 g (86%) of the title compound: mass spectrum (ion spray): m/z=279.1 (M+1).

Workup

  1. additionPour the mixture onto ice chips
  2. customRemove the resulting orange precipitate
  3. filtrationby vacuum filtration
  4. customdry it under vacuum

Sources & evidence

ORD record
ord-248a6419fc0248d1a6533b59d9593bae
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

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