Triethylamine → benzyl N-(2-bromoethyl)carbamate

HRID 565448Notes

Reaction equation

HRID 565448 reaction equation
Cl.[Br:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([O:20][C:21]([NH:5][CH2:4][CH2:3][Br:2])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 122086202-BROMOETHYLAMINE HYDROCHLORIDE

Product 1

HCID 278694benzyl N-(2-bromoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromoethylamine hydrochloride (25 g: a product of Tokyo Kasei Kogyo Co., Ltd.) and triethylamine (34 ml) in methylene chloride (450 ml), benzyloxycarbonyl chloride (19 ml) was added dropwise over a period of 20 minutes and the mixture was agitated at room temeprature for 19 hours. The resulting reaction mixture was washed with water, with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride succeedingly, whereupon the separated organic layer was dried and, then, removed off the solvent by distilling it of under reduced pressure. The residue was cooled with ice and the crystals were collected by filtration and washed with hexane, whereby the above-identified compound was obtained (29.4 g).

Workup

  1. customThe resulting reaction mixture
  2. washwas washed with water, with saturated aqueous sodium bicarbonate solution and with saturated aqueous sodium chloride succeedingly
  3. customwhereupon the separated organic layer was dried
  4. customremoved off the solvent
  5. distillationby distilling it of under reduced pressure
  6. temperatureThe residue was cooled with ice
  7. filtrationthe crystals were collected by filtration
  8. washwashed with hexane, whereby the above-identified compound
  9. customwas obtained (29.4 g)

Sources & evidence

ORD record
ord-fa2d5f80336c4406bea3c9af26d39792
Source dataset
uspto-grants-2001_01
Patent number
US06172099B2

Reaction notes

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