Ethanol → Unii-9tvu6uuo09

HRID 49528Notes

Reaction equation

HRID 49528 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:25][CH3:26])=[C:9]([CH:24]=1)[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[O:11])(=[O:3])N.C([OH:29])C.[OH-].[Na+].O>C(OCC)C>[CH3:26][O:25][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:1]([OH:29])=[O:3])=[CH:24][C:9]=1[C:10](=[O:11])[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 120946625-carbamoylmethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

Product 1

HCID 9799335Unii-9tvu6uuo09

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 700 mg of 5-carbamoylmethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide were added 21 ml of ethanol, 7 ml of 1 mol/l aqueous solution of sodium hydroxide, and the mixture was refluxed for 18 hours. The reaction mixture was poured into water, washed with ethyl acetate, and further the aqueous layer was adjusted to pH value of 1 to 2 with 2 mol/l hydrochloric acid, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated brine in sequence and dried again over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the residue obtained was suspended with diethyl ether to collect the crystals by filtration. The crystals obtained were recrystallized from methylene chloride to obtain 435 mg of aimed product as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. washwashed with ethyl acetate
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine in sequence
  5. dry with materialdried again over anhydrous sodium sulfate
  6. distillationSolvent was distilled off under reduced pressure
  7. customthe residue obtained
  8. customto collect the crystals
  9. filtrationby filtration
  10. customThe crystals obtained
  11. customwere recrystallized from methylene chloride

Sources & evidence

ORD record
ord-8bbdcd7f42744919a823864bb298ee42
Source dataset
uspto-grants-2004_03
Patent number
US06706763B1

Reaction notes

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