Isopropyl chloroformate → HCID 86587682, compound

HRID 1836613Notes

Reaction equation

HRID 1836613 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].Cl[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8].C(N(CC)CC)C>ClCCl>[CH:10]([O:9][C:7](=[O:8])[NH:5][CH2:4][CH2:3][Br:2])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 86587682HCID 86587682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of bromoethylamine hydrobromide (5.0 g, 24.4 mmol), isopropyl chloroformate (1.0 M in tetrahydrofuran, 16.3 ml, 16.3 mmol), and anhydrous dichloromethane (100 ml) was treated with triethylamine (4.5 ml, 33 mmol) and stirred at ambient temperature for 18 hr. The mixture was diluted with dichloromethane (200 ml), washed with 1 M hydrochloric acid, 1 M sodium hydroxide, and brine, dried over sodium sulfate and evaporated to give (2-bromo-ethyl)-carbamic acid isopropyl ester clear oil. 1H-NMR δ(CDCl3) 5.01 (1H, br s), 4.92 (m, 1 H), 3.58 (m, 2 H), 3.48 (m, 2 H), 1.25 (m, 6 H).

Workup

  1. washwashed with 1 M hydrochloric acid, 1 M sodium hydroxide, and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-d7b8ec8a286b413190696307bb9f00cb
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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