3-Bromobenzylamine hydrochloride → N-(3-Bromobenzyl)-2,2-diethoxyacetimidamide

HRID 250136

Reaction equation

HRID 250136 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH2:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.C[O-].[Na+].[CH2:14]([O:16][CH:17]([O:22][CH2:23][CH3:24])[C:18](=[NH:21])OC)[CH3:15]>CO>[Br:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH2:9][NH:10][C:18](=[NH:21])[CH:17]([O:22][CH2:23][CH3:24])[O:16][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 27249803-Bromobenzylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 17874536Methyl 2,2-diethoxyethanecarboximidate

Product 1

HCID 178471669N-(3-Bromobenzyl)-2,2-diethoxyacetimidamideYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3-Bromophenyl)methanamine hydrochloride (3.62 g, 15.64 mmol) and sodium methoxide (3.58 mL, 15.64 mmol) were added to a solution of methyl 2,2-diethoxyacetimidate (5.042 g, 31.3 mmol) in methanol (15 mL). The cloudy mixture was heated at 70 C for 1.5 h and the resulting yellow mixture was concentrated. The residue was purified by silica gel chromatography with 100% ethyl acetate. The desired fractions were concentrated to give a yellow viscous oil (2.5 g, 51%). LCMS:R.T.=2.11; [M+2]+=317.06.

Workup

  1. temperatureThe cloudy mixture was heated at 70 C for 1.5 h
  2. concentrationthe resulting yellow mixture was concentrated
  3. customThe residue was purified by silica gel chromatography with 100% ethyl acetate
  4. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-b952617a9aa44a4e9eb784faa5eb642a
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Linked notes

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