Acetone → benzyl N-(2-bromoethyl)carbamate

HRID 1381965Notes

Reaction equation

HRID 1381965 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.[Br:16][CH2:17][CH2:18][NH2:19]>[OH-].[Na+]>[CH2:1]([O:8][C:9]([NH:19][CH2:18][CH2:17][Br:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 78512-BromoethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 278694benzyl N-(2-bromoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.46 mol (78.5 g) of benzyloxycarbonyl chloride in 1 volume of acetone is added slowly to a solution of 0.45 mol (92.2 g) of 2-bromoethylamine in 1 liter of nomal sodium hydroxide solution. When the reaction has ended (about 48 hours), the acetone is evaporated off under reduced pressure and the residue is then acidified to between pH 1 and 2 and extracted with ether. Benzyloxycarbonylamino-2-bromoethane is obtained after evaporation. This product is reacted with N-hydroxyphthalimide following the procedure of Example 1-a to give N-2-benzyloxycarbonylaminoethoxyphthalimide in the form of white crystals melting at 95° C. with a yield of 73%. After treatment with hydrazine under the conditions of Example 1-a, 2-benzyloxycarbonylaminoethoxyamine hydrochloride melting at 178° C. is obtained (yield=95% relative to the phthalimide).

Workup

  1. custom(about 48 hours)
  2. customthe acetone is evaporated off under reduced pressure
  3. extractionextracted with ether

Sources & evidence

ORD record
ord-91aa1d5e3c6741c3b4fb077036bbb8b9
Source dataset
uspto-grants-1989_02
Patent number
US04804684

Reaction notes

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