Methyl cyanoacetate → HCID 15068773, compound

HRID 1110436Notes

Reaction equation

HRID 1110436 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[H-].[Na+].[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>C1COCC1>[CH3:7][O:6][C:4](=[O:5])[CH:3]([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:1]#[N:2]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 24758Sodium hydrideHCID 737684-(Trifluoromethyl)phenyl isocyanate

Product 1

HCID 15068773HCID 15068773, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The anion of methyl cyanoacetate (2.20 g, 22.2 mmoles) was made at 0° C. using sodium hydride (0.8 g, 22 mmoles) in 70 ml of THF and treated dropwise with 4-trifluoromethylphenyl isocyanate (4.1 g, 22 mmoles). After one hour at 0° C. the solvent was removed and the residue was partitioned between 1N HCl and ethyl acetate. The organic layer was washed with brine, dried and partially concentrated in vacuo to precipitate the title compound (3.8 g) as a white solid, mp 186°-189° C.

Workup

  1. customwas made at 0° C.
  2. customAfter one hour at 0° C. the solvent was removed
  3. customthe residue was partitioned between 1N HCl and ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationpartially concentrated in vacuo
  7. customto precipitate the title compound (3.8 g) as a white solid, mp 186°-189° C.

Sources & evidence

ORD record
ord-4f61cbf2f6c2439bac32e7e1078882c9
Source dataset
uspto-grants-1990_12
Patent number
US04975462

Reaction notes

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