Sodium Chloride → HCID 12090302, compound

HRID 1168035Notes

Reaction equation

HRID 1168035 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][CH3:22])=[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][CH3:22]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 27249803-Bromobenzylamine hydrochloride

Product 1

HCID 12090302HCID 12090302, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10.00 g of 3-bromobenzylamine hydrochloride suspended in chloroform (100 ml) was mixed with 9.55 g of triethylamine at room temperature. The resulting solution was stirred under cooling with ice while 4.67 g of methyl 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 9.54 g of methyl N-(3-bromobenzyl)carbamate as white crystals. m.p. 41-44° C.

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-843bda6c90424b4391826737afe549f1
Source dataset
uspto-grants-2003_09
Patent number
US06620961B1

Reaction notes

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