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

HRID 1596458Notes

Reaction equation

HRID 1596458 reaction equation
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Br.[Br:13][CH2:14][CH2:15][NH2:16]>O1CCOCC1.[OH-].[Na+].O1CCOCC1>[CH2:4]([O:3][C:1](=[O:2])[NH:16][CH2:15][CH2:14][Br:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 278694benzyl N-(2-bromoethyl)carbamateYield 92%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 18323598NaOH dioxaneSolvent

Procedure

A solution of CBz-Cl (7.7 mL; 54 mmol) in dioxane (5 mL) was added to a cold (0° C.) stirred solution of 2-bromoethylamine hydrobromide (10.0 g; 49 mmol) in 40 mL 1M NaOH:dioxane (3:1) under Schotten-Bauman conditions. The reaction mixture was allowed to attain rt. and extracted with CHCl3. The organic layer was separated, concentrated and purified by column chromatography (CHCl3) to give the sub-title compound in a 92% yield.

Workup

  1. customto attain rt
  2. extractionand extracted with CHCl3
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. custompurified by column chromatography (CHCl3)

Sources & evidence

ORD record
ord-0734068bfeb844ec94cec84a9b0230f2
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

Loading…