Water → phenyl N-(4-benzoylphenyl)carbamate

HRID 1935689Notes

Reaction equation

HRID 1935689 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[C:16](Cl)(=[O:24])[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>N1C=CC=CC=1>[C:6]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:16](=[O:24])[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:14]=1)(=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 143464-AminobenzophenoneHCID 15891Phenyl chloroformate

Product 1

HCID 15548170phenyl N-(4-benzoylphenyl)carbamateYield 110.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-aminobenzophenone (1.97 g) dissolved in pyridine (50 mL), phenyl chlorocarbonate (1.38 g) was added at 0° C. and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2) to give the subject compound (3.1 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2)

Sources & evidence

ORD record
ord-28c6d3ba5d5841afaaa157be20589d7c
Source dataset
uspto-grants-2002_05
Patent number
US06388077B1

Reaction notes

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