Cyanoacetamide → HCID 178509569, compound

HRID 2272459Notes

Reaction equation

HRID 2272459 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].CN(C)[CH:9]=[CH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=O.[H-].[Na+]>CN(C=O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH:10]=[CH:9][C:3]([C:1]#[N:2])=[C:4]([OH:5])[N:6]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 6005393-(Dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one

Product 1

HCID 178509569HCID 178509569, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Cyanoacetamide (4.31 g) and 3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one (9.00 g) were added in this order to a mixture of sodium hydride (60% oil, 4.10 g) and DMF (90 mL), and the resultant mixture was stirred at 105 C for 2 hours. The solvent was distilled off. Water was added to the obtained residue, and then, the mixture was rendered acidic by the addition of acetic acid and stirred at 70 C for 15 minutes. Methanol was added to the reaction mixture for suspension, and the deposited solid was washed with ethyl acetate to obtain the title compound (9.98 g).

Workup

  1. distillationThe solvent was distilled off
  2. additionWater was added to the obtained residue
  3. additionthe mixture was rendered acidic by the addition of acetic acid
  4. additionMethanol was added to the reaction mixture for suspension
  5. washthe deposited solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-d76310f48f1e4ff58e8f918e7420df7b
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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