Sodium hydride → beta-Methylamino-beta-oxo-alpha-(4-trifluoromethylphenyl) carbamoylpropionitrile

HRID 1110437Notes

Reaction equation

HRID 1110437 reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5](=[O:9])[CH2:6][C:7]#[N:8].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1>CCCCCC.C1COCC1>[CH3:3][NH:4][C:5](=[O:9])[CH:6]([C:19](=[O:20])[NH:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([F:10])([F:22])[F:21])=[CH:13][CH:14]=1)[C:7]#[N:8]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 806222-Cyano-N-methylacetamide

Product 1

HCID 15068774beta-Methylamino-beta-oxo-alpha-(4-trifluoromethylphenyl) carbamoylpropionitrileYield 62.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Sodium hydride (0.82 g, 20.4 mmoles), washed with Skellysolve B, was suspended in 20 ml of dry THF and treated at 15° C. with N-methylcyanoacetamide (2.0 g, 20.4 mmoles) [prepared in Step A]. The resultant suspension was further cooled to 5° C. and 4-trifluoromethylphenyl isocyanate (3.80 g, 20.4 mmoles) was added over several minutes. After 18 h at ambient temperature the solvent was removed and the residual syrup was poured into a cold mixture of water and 4 ml of 6N HCl. The precipitate was isolated by filtration and recrystallized from ethanol to give 3.63 g of the title compound, mp 184°-186° C.

Workup

  1. customAfter 18 h at ambient temperature the solvent was removed
  2. additionthe residual syrup was poured into a cold mixture of water and 4 ml of 6N HCl
  3. customThe precipitate was isolated by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-48aed9ddb9324b03b4187261a6ea32b6
Source dataset
uspto-grants-1990_12
Patent number
US04975462

Reaction notes

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