Potassium Hydroxide → 5-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile

HRID 624539Notes

Reaction equation

HRID 624539 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:9])=[CH:5][C:6]=1[C:7]#[N:8].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[OH-].[K+]>CS(C)=O.O>[CH3:9][C:4]1[S:3][C:2]([NH:1][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])=[C:6]([C:7]#[N:8])[CH:5]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 738951-Fluoro-2-nitrobenzeneHCID 6890562-Amino-5-methyl-3-thiophenecarbonitrile

Product 1

HCID 3954605-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-amino-5-methylthiophene-3-carbonitrile (13.8 g, 100 mmol) and 1-fluoro-2-nitrobenzene (16.92 g, 120 mmol) in dimethylsulfoxide was added potassium hydroxide (11.2 g, 200 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with water, and the resulting suspension was filtered. The filtered cake was dried to give 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carbonitrile as a red solid used without further purification. 1H NMR: (400 MHz, CDCl3) δ 9.69 (s, 1H), 8.27-8.25 (m, 1H), 7.56-7.52 (m, 1H), 7.23-7.20 (m, 1H), 7.0-6.96 (m, 1H), 6.80 (s, 1H), 2.49 (s, 3H).

Workup

  1. filtrationthe resulting suspension was filtered
  2. customThe filtered cake was dried

Sources & evidence

ORD record
ord-cd2e92d6cd954234a1d90926a6fa93c0
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

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