Sodium hydride → 5-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile

HRID 483966

Reaction equation

HRID 483966 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[S:15][C:16]([CH3:21])=[CH:17][C:18]=1[C:19]#[N:20]>O1CCCC1>[N+:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH:13][C:14]1[S:15][C:16]([CH3:21])=[CH:17][C:18]=1[C:19]#[N:20])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 6890562-Amino-5-methyl-3-thiophenecarbonitrile

Product 1

HCID 3954605-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrileYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred slurry of sodium hydride (14.4 g, 50% dispersion in oil, 0.3 mol) in dry tetrahydrofuran (50 mL) under nitrogen was added, dropwise, a solution of 2-fluoronitrobenzene (28.2 g, 0.2 mol) and 2-amino-5-methylthiophene3-carbonitrile (27.6 g, 0.2 mol) in dry tetrahydrofuran (250 mL). The mixture was stirred at 25° C. for 24 hours, poured onto cracked ice and extracted into dichloromethane (3×500 mL). The combined extracts were washed with 2N hydrochloric acid (2×200 mL), water (2×200 mL), dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was crystallised from ethanol to give the title compound, (35.2 g), m.p. 99°-102° C.

Workup

  1. additionpoured
  2. extractionextracted into dichloromethane (3×500 mL)
  3. washThe combined extracts were washed with 2N hydrochloric acid (2×200 mL), water (2×200 mL)
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-cedef290daa04390ad9a871c710b93f5
Source dataset
uspto-grants-1993_07
Patent number
US05229382

Linked notes

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