Ethylamine → benzyl N-ethylcarbamate

HRID 1920006Notes

Reaction equation

HRID 1920006 reaction equation
[CH2:1]([NH2:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>C(Cl)Cl>[CH2:17]([O:16][C:14](=[O:15])[NH:3][CH2:1][CH3:2])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 10387Benzyl chloroformateHCID 81531Diisopropylethylamine

Product 1

HCID 12384304benzyl N-ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethylamine (1.3 mL, 20.0 mmol) and diisopropylethylamine (7 mL, 40.0 mmol) were combined in CH2Cl2 (200 mL) and cooled to 0° C. Benzyl chloroformate (2.86 mL, 20.0 mmol) was added dropwise, and the reaction was stirred at 0° C. for 30 minutes. Once no starting material was seen by analytical tlc, the mixture was warmed to room temperature and washed with H2O, 0.1N aqueous HCl, and H2O, and then dried and concentrated to give the title compound.

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. washwashed with H2O, 0.1N aqueous HCl, and H2O
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-adb3994c054e4e9aa7c02a0dc0c5eebb
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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