Phenyl chloroformate → Ethyl N-phenylcarbamate

HRID 1756496Notes

Reaction equation

HRID 1756496 reaction equation
C(C1C=CC([CH:15]2[CH:20]([NH2:21])[CH2:19][CH:18]=[CH:17][CH2:16]2)=CC=1)=CC1C=CC=CC=1.Cl[C:23]([O:25][C:26]1C=CC=C[CH:27]=1)=[O:24]>C(Cl)Cl.N1C=CC=CC=1>[C:20]1([NH:21][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 53872197HCID 53872197, compound

Product 1

HCID 7591Ethyl N-phenylcarbamateYield 170.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-(4'-styrylphenyl)cyclohex-3-enylamine (0.44 g, 1.66 mmol) in methylene chloride (21 mL) and pyridine (10 mL) at 0° C. is added phenyl chloroformate (0.25 g, 1.6 mmol). The reaction is warmed to room temperature and partitioned between methylene chloride and water. The organic extracts are washed with brine, dried (MgSO4) and evaporated. The residue is triturated with diethyl ether and purified by flash chromatography (2% diethyl ether/toluene) to give the intermediate phenyl urethane (0.45 g, 70%); Rf=0.26. MS (FAB+ion) m/z 396 (M+H).

Workup

  1. custompartitioned between methylene chloride and water
  2. washThe organic extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue is triturated with diethyl ether
  6. custompurified by flash chromatography (2% diethyl ether/toluene)

Sources & evidence

ORD record
ord-011d60789c224fbe81444eaa6a2485ab
Source dataset
uspto-grants-1995_08
Patent number
US05441946

Reaction notes

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