Sodium ethoxide → HCID 13752588, compound

HRID 845397Notes

Reaction equation

HRID 845397 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])=O)=[CH:4][CH:3]=1.CC[O-].[Na+].[Na]>C(O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:9](=[O:10])[CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 13752587HCID 13752587, compound

Product 1

HCID 13752588HCID 13752588, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a refluxed solution of 40 g of 2-(4-fluorobenzoyl)acetanilide in 300 ml of ethanol, a sodium ethylate solution, prepared from 9.13 g of sodium and 150 ml of ethanol, is added dropwise over a period of 2 hours. The reaction mixture is refluxed for 20 minutes, allowed to cool and poured onto ice-water. The precipitate is collected, dried and recrystallized from chloroform - diethyl ether to give 31.3 g of the title compound, m.p. 247°-248° C.

Workup

  1. additionis added dropwise over a period of 2 hours
  2. temperatureThe reaction mixture is refluxed for 20 minutes
  3. temperatureto cool
  4. additionpoured onto ice-water
  5. customThe precipitate is collected
  6. customdried
  7. customrecrystallized from chloroform - diethyl ether

Sources & evidence

ORD record
ord-d21f07191d27400ea2cee9a5bd144246
Source dataset
uspto-grants-1988_07
Patent number
US04758566

Reaction notes

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