Cyanoacetamide → HCID 178509569, compound

HRID 530992Notes

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

Conditions

Temperature: 70 °C

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

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

Sources & evidence

ORD record: ord-d6eae966e8664365b60c6cd1a39fde7e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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