Sodium hydride → Methyl 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carboxylate

HRID 483968Notes

Reaction equation

HRID 483968 reaction equation
[H-].[Na+].[NH2:3][C:4]1[S:5][C:6]([CH3:13])=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10].F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22]>O1CCCC1>[N+:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:3][C:4]1[S:5][C:6]([CH3:13])=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10])([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 675878Methyl-2-amino-5-methyl-3-thiophenecarboxylate

Product 1

HCID 19592005Methyl 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred suspension of sodium hydride (2 g) in dry tetrahydrofuran (25 mL) under a nitrogen atmosphere was added a solution of methyl 2-amino-5-methylthiophene-3-carboxylate (4.8 g, 0.028 mol) and 2-fluoronitrobenzene (4.0 g, 0.025 mol) in dry tetrahydrofuran (30 mL). The mixture was stirred at 25° C. for 20 hours, poured onto ice and partitioned between 2N hydrochloric acid and ethyl acetate. The organic extracts were dried over magnesium sulphate, the solvent was evaporated under reduced pressure and the title compound purified by chromatography on silica gel, eluted with toluene, and crystallised from ethanol (4.1 g).

Workup

  1. additionpoured onto ice
  2. custompartitioned between 2N hydrochloric acid and ethyl acetate
  3. dry with materialThe organic extracts were dried over magnesium sulphate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe title compound purified by chromatography on silica gel
  6. washeluted with toluene
  7. customcrystallised from ethanol (4.1 g)

Sources & evidence

ORD record
ord-308d214c725e4e9d8c68673f1534a0a4
Source dataset
uspto-grants-1993_07
Patent number
US05229382

Reaction notes

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