Sodium Chloride → isopropyl N-(3-bromobenzyl)carbamate

HRID 1168036

Reaction equation

HRID 1168036 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].C(N(CC)CC)C.Cl[C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20].[Cl-].[Na+]>C(Cl)(Cl)Cl>[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:7][C:19](=[O:20])[O:21][CH:22]([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 27249803-Bromobenzylamine hydrochloride

Product 1

HCID 12090304isopropyl N-(3-bromobenzyl)carbamateYield 90.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.00 g of 3-bromobenzylamine hydrochloride suspended in chloroform (20 ml) was mixed with 2.86 g of triethylamine at room temperature. The resulting solution was stirred under cooling with ice while 1.82 g of isopropyl chloroformate was added dropwise and then stirred at room temperature for 2 hours. After the reaction, the reaction solution was poured into saturated aqueous sodium chloride, and the organic layer was separated, dried over anhydrous magnesium sulfate and evaporated at ordinary pressure for removal of the solvent. The residue was purified by silica gel column chromatography to give 3.33 g of isopropyl N-(3-bromobenzyl)carbamate as a colorless transparent viscous liquid.

Workup

  1. additionwas added dropwise
  2. stirringstirred at room temperature for 2 hours
  3. customAfter the reaction
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated at ordinary pressure for removal of the solvent
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d5a46ed7fa154935be9f3f2e46b15040
Source dataset
uspto-grants-2003_09
Patent number
US06620961B1

Linked notes

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