Acetic Acid → HCID 69063437, compound

HRID 730431Notes

Reaction equation

HRID 730431 reaction equation
[K].[CH:2]([CH:4]([CH2:7][C:8]#[N:9])[C:5]#[N:6])=O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[NH2:18])=[CH:13][CH:12]=1.C(O)(=O)C>O>[F:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]([NH:18]/[CH:2]=[C:4](\[CH2:7][C:8]#[N:9])/[C:5]#[N:6])[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 109550394-Fluoro-alpha-(4-fluorophenyl)benzenemethanamineHCID 86606793HCID 86606793, compound

Product 1

HCID 69063437HCID 69063437, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of formyl succinonitrile potassium salt (6.67 g, 45.6 mmol) and 1,1-bis(4-fluorophenyl) methaneamine (11.0 g, 50.2 mmol) in water (19 ml) was added acetic acid (19 ml) at room temperature, and the mixture was stirred 100° C. for 30 minutes. The solvent was distilled off under reduced pressure. The residue was poured into iced water, made basic with potassium carbonate and then extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give the objective product as oily matter. Yield (amount) 14.0 g, yield (rate) 99.3%

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionThe residue was poured into iced water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto give the objective product as oily matter
  8. customYield (amount) 14.0 g
  9. customyield (rate) 99.3%

Sources & evidence

ORD record
ord-96fc6d4be570439583138995162dc8a3
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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