Water → HCID 9881943, compound

HRID 1003414Notes

Reaction equation

HRID 1003414 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[O:14][CH2:15][CH2:16][CH3:17])=O.[C:19]([CH2:21][C:22]([NH2:24])=[O:23])#[N:20].C[O-].[Na+].O>CN(C)C=O.C(O)(=O)C>[C:19]([C:21]1[C:22](=[O:23])[NH:24][C:5]([C:7]2[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=2[O:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1)#[N:20]

Participants

7

Reactant 4

HCID 962WaterHCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 54287555HCID 54287555, compound

Product 1

HCID 9881943HCID 9881943, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 3-dimethylamino-1-(5-fluoro-2-propoxyphenyl)-2-propene-1-one (2.46 g), cyanoacetamide (0.93 g), sodium methoxide (from 50% sodium hydride, 1.69 g, and methanol, 0.85 ml) in dimethylformamide (20 ml) was heated under reflux for 7 hours. The mixture was poured into water (150 ml) and acetic acid added to pH 4 to give a crude product. Recrystallization twice from acetonitrile gave a solid, 0.68 g, which was washed with petroleum ether and recrystallized again from acetonitrile to give the pure title compound, 0.15 g, m.p. 242-243° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. additionadded to pH 4
  4. customto give a crude product
  5. customRecrystallization twice from acetonitrile
  6. customgave a solid, 0.68 g, which
  7. washwas washed with petroleum ether
  8. customrecrystallized again from acetonitrile

Sources & evidence

ORD record
ord-eb6150c1718141dd9d3692e3377fc27d
Source dataset
uspto-grants-2000_04
Patent number
US06046216

Reaction notes

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