Sodium hydride → HCID 58625993, compound

HRID 131304Notes

Reaction equation

HRID 131304 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:9][CH3:10])=[CH:5][C:6]=1[C:7]#[N:8].F[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].[H-].[Na+]>O1CCCC1>[F:18][C:16]1[CH:15]=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[C:12]([NH:1][C:2]2[S:3][C:4]([CH2:9][CH3:10])=[CH:5][C:6]=2[C:7]#[N:8])[CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 679672,4-DifluoronitrobenzeneHCID 156801192-Amino-5-ethylthiophene-3-carbonitrile

Product 1

HCID 58625993HCID 58625993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 2-amino-5-ethyl-thiophene-3-carbonitrile (8.2 g, 54 mmol) and 2,4-difluoronitrobenzene (8.6 g, 54 mmol) in tetrahydrofuran (20 ml) and add to a stirring solution of sodium hydride (50% dispersion in mineral oil)(4.1 g, 1.4 equiv) in tetrahydrofuran (50 ml) under a nitrogen atmosphere. Maintain the rate of addition to keep the temperature below 45° C. and gas evolution under control. Stir 18 h. Pour the mixture into a mixture of ice and 2NHCl, extract into ethyl acetate, dry (MgSO4) and concentrate under reduced pressure. Dissolve in ethanol (100 ml) and collect 2-(5-fluoro-2-nitro-phenylamino)-5-ethyl-thiophene-3-carbonitrile by filtration as a yellow solid (7.9 g, 50%): mass spectrum (LCMS) 292 (M+1), 314 (M+Na). NMR (1H, 300 MHz, CDCl3): δ 9.7 (1H broad), 8.25 (1H,m), 6.80 (1H, s), 6.75 (1H,dd), 6.65 (1H, s), 2.80 (2H,q), 1.35(3H,t).

Workup

  1. temperatureMaintain
  2. additionthe rate of addition
  3. customthe temperature below 45° C. and gas evolution
  4. additionPour the mixture
  5. additioninto a mixture of ice and 2NHCl
  6. extractionextract into ethyl acetate
  7. dry with materialdry (MgSO4)
  8. concentrationconcentrate under reduced pressure
  9. dissolutionDissolve in ethanol (100 ml)
  10. customcollect 2-(5-fluoro-2-nitro-phenylamino)-5-ethyl-thiophene-3-carbonitrile
  11. filtrationby filtration as a yellow solid (7.9 g, 50%)

Sources & evidence

ORD record
ord-bb9532a3f07a473ba7e423d608d90cee
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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