Ammonia → 4-Benzyloxybenzamide

HRID 854693

Reaction equation

HRID 854693 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH3:24]>C1COCC1.CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:24])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 738804-(Benzyloxy)benzoic acid

Product 1

HCID 27264314-Benzyloxybenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 4.565 g (20 mmol) 4-benzyloxybenzoic acid in 25 ml THF and 0.3 ml N,N-dimethylformamide was added dropwise at 0° C. a solution of 2.6 ml oxalyl chloride in 5 ml THF. Stirring was continued for 3 hours at room temperature, then the suspension was added slowly to a stirred ice-cold solution of concentrated aqueous ammonia. The organic solvent was evaporated, 100 ml water added and the precipitate isolated and dried in vacuo at 50° C. Yield: 4.29 g (94%) white solid.

Workup

  1. customThe organic solvent was evaporated
  2. addition100 ml water added
  3. customthe precipitate isolated
  4. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-2827dab36d9049db89be51250fb6c366
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Linked notes

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