Cyanoacetamide → 2-(2-Amino-4-nitrophenyl)-2-cyanoacetamide

HRID 216613

Reaction equation

CC(C)([O-])C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].F[C:14]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=1[NH2:16].[Cl-].[NH4+]>CN(C)C=O>[NH2:16][C:15]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:14]=1[CH:9]([C:7]#[N:8])[C:10]([NH2:12])=[O:11]

Participants

Conditions

Temperature: 5 °C

Procedure

Potassium tert-butoxide (36 g, 0.32 mol) was added to a solution of 2-cyanoacetamide (27 g, 0.32 mol) in anhydrous N,N-dimethylformamide (700 mL), and a solution of 2-fluoro-5-nitroaniline (25 g, 0.16 mol) in anhydrous N,N-dimethylformamide (80 mL) was added dropwise thereto under ice-cooling. After the reaction mixture was stirred at 5° C. for 18 hours, it was poured into a saturated ammonium chloride aqueous solution (1.0 L) under ice-cooling. The whole was extracted with ethyl acetate (1.0 L). The organic layer was washed with water (500 mL), brine (300 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, toluene (100 mL) and dichloromethane (100 mL) were added to the residue. The precipitated solid was filtered off, and dried under reduced pressure to give the title reference compound (33 g) as a brown solid (yield 94%).

Workup

temperatureunder ice-cooling
temperaturecooling
extractionThe whole was extracted with ethyl acetate (1.0 L)
washThe organic layer was washed with water (500 mL), brine (300 mL)
dry with materialdried over anhydrous magnesium sulfate
customAfter the solvent was evaporated under reduced pressure, toluene (100 mL) and dichloromethane (100 mL)
additionwere added to the residue
filtrationThe precipitated solid was filtered off
customdried under reduced pressure

Sources & evidence

ORD record: ord-953f7f56d69d4386834a259c4141091a
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193237B2

Linked notes

Loading…