Triethylamine → benzyl N-(2-bromoethyl)carbamate

HRID 747660Notes

Reaction equation

HRID 747660 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>ClCCl>[CH2:17]([O:16][C:14](=[O:15])[NH:5][CH2:4][CH2:3][Br:2])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 278694benzyl N-(2-bromoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10 g (49 mmol) of 2-bromoethylamine hydrobromide and 15 ml of triethylamine were dissolved in dichloromethane. 7.8 ml (49 mmol) of benzyl chloroformate was added to the obtained solution under cooling with ice, and they were stirred at room temperature. The reaction mixture was treated with dichloromethane as the extractant in an ordinary manner to obtain a crude product, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. customto obtain a crude product, which
  3. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-1e5b52f86ad04e97a3127dac4b430d26
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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