Hydrochloric Acid → benzyl N-phenyl-N-(prop-2-en-1-yl)carbamate

HRID 2299635Notes

Reaction equation

HRID 2299635 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].Cl>ClCCl>[CH2:1]([N:4]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10387Benzyl chloroformateHCID 68525N-Allylaniline

Product 1

HCID 11448535benzyl N-phenyl-N-(prop-2-en-1-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, to a solution of allylphenylamine (3 ml) in dichloromethane (30 ml) were added pyridine (2.1 ml) and benzyl chloroformate (3.5 ml) at 5° C., and the mixture was stirred at the same temperature for 3 hours. The resulting mixture was poured into aqueous 1N hydrogen chloride and extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1 to 10:1) to give N-allyl-N-phenylbenzyloxycarbonylamine (5.5 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-79f27e781d60470e98b922363b30c5ef
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

Loading…