Ammonia → N-[2-(3-cyanophenoxy)ethyl]-4-carbamoylbenzamide

HRID 747663Notes

Reaction equation

HRID 747663 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[O:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=1)=[O:11])#[N:2].[NH3:25]>>[C:1]([C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[O:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[C:12]1[CH:21]=[CH:20][C:15]([C:16](=[O:17])[NH2:25])=[CH:14][CH:13]=1)#[N:2]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 68830761methyl 4-[N-[2-(3-cyanophenoxy)ethyl)carbamoyl]benzoate

Product 1

HCID 68835528N-[2-(3-cyanophenoxy)ethyl]-4-carbamoylbenzamide

Procedure

100 mg (0.31 mmol) of methyl 4-[N-[2-(3-cyanophenoxy)ethyl)carbamoyl]benzoate was stirred in 100 ml of 28% aqueous ammonia overnight. The reaction liquid was evaporated under reduced pressure, and 1 N hydrochloric acid was added to the residue. After the extraction with ethyl acetate, the organic layer was washed with saturated aqueous NaCl solution and then dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain the title compound.

Workup

  1. customThe reaction liquid
  2. customwas evaporated under reduced pressure, and 1 N hydrochloric acid
  3. additionwas added to the residue
  4. extractionAfter the extraction with ethyl acetate
  5. washthe organic layer was washed with saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8fb0f1d5eebf44a795ebaed067c60749
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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