Triethylamine → tert-Butyl N-(2-bromoethyl)carbamate

HRID 2398226Notes

Reaction equation

HRID 2398226 reaction equation
[N:1]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[N+]=[N-].C(N(CC)CC)C.Br.[Br:19][CH2:20][CH2:21]N>C(Cl)Cl>[C:4]([NH:1][CH2:21][CH2:20][Br:19])([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of t-butyl azidoformate (15.81 g) and triethylamine (30 ml) was added dropwise to a stirred suspension of 2-bromoethylamine hydrobromide (20.5 g.); in methylene chloride (100 ml.). The mixture was stirred for 3 hr., then filtered. The filtrate was concentrated to a small volume, and the residue was distributed between ether and water. The ether layer was dried, then distilled under reduced pressure, collecting the fraction b.p. 92°-94°/0.9 mm as N-carbo-t-butoxy-2-bromoethylamine (1.756 g.)

Workup

  1. filtration, then filtered
  2. concentrationThe filtrate was concentrated to a small volume
  3. dry with materialThe ether layer was dried
  4. distillationdistilled under reduced pressure
  5. customcollecting the fraction b.p. 92°-94°/0.9 mm as N-carbo-t-butoxy-2-bromoethylamine (1.756 g.)

Sources & evidence

ORD record
ord-ae9156ad5f754b78bf104bca5bbbe623
Source dataset
uspto-grants-1977_05
Patent number
US04024137

Reaction notes

Loading…