Water → phenyl N-(4-benzoylphenyl)carbamate

HRID 1249818Notes

Reaction equation

HRID 1249818 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-95d2f82da1264306a5d28596ee9fafe0
Source dataset
uspto-grants-2002_01
Patent number
US06335345B1

Reaction notes

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