Benzyl chloroformate → benzyl N-(2-bromoethyl)carbamate

HRID 894369Notes

Reaction equation

HRID 894369 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].[CH2:6]([O:13][C:14](Cl)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>O>[C:14]([NH:5][CH2:4][CH2:3][Br:2])([O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 278694benzyl N-(2-bromoethyl)carbamateYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Twenty point five g (0.10 mole) of 2-bromoethylamine hydrobromide was dissolved in 140 ml of water. At 0° C., 15.3 g (0.089 mole) of benzylchloroformate was added, followed by 18.5 g (0.1 moles) of sodium bicarbonate, and the mixture was stirred for 15 minutes at 0°. The mixture was then stirred overnight at room temperature. The mixture was extracted with diethylether (3×250 ml), the combined portions of which were washed thrice with 150 ml portions of saturated sodium bicarbonate, dried with magnesium sulfate and evaporated to yield 20.98 g of the crude N-carbobenzyloxy-2-bromoethylamine (NCBA).

Workup

  1. stirringThe mixture was then stirred overnight at room temperature
  2. extractionThe mixture was extracted with diethylether (3×250 ml)
  3. washthe combined portions of which were washed thrice with 150 ml portions of saturated sodium bicarbonate
  4. dry with materialdried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-48c950c4be7c48a5bc8d8f109f10ecea
Source dataset
uspto-grants-1981_08
Patent number
US04283434

Reaction notes

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