(3-Chloro-2-fluorophenyl)methanamine → N-(3-chloro-2-fluorobenzyl)-2,2-diethoxyacetimidamide

HRID 1876008Notes

Reaction equation

HRID 1876008 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH2:8][NH2:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11]([O:13][CH:14]([O:19][CH2:20][CH3:21])[C:15](=[NH:18])OC)[CH3:12]>CO>[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][NH:9][C:15](=[NH:18])[CH:14]([O:19][CH2:20][CH3:21])[O:13][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 2773614(3-Chloro-2-fluorophenyl)methanamineHCID 17874536Methyl 2,2-diethoxyethanecarboximidate

Product 1

HCID 178471672N-(3-chloro-2-fluorobenzyl)-2,2-diethoxyacetimidamideYield 71.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3-Chloro-2-fluorophenyl)methanamine (1.0 g, 6.27 mmol) was added to a solution of methyl 2,2-diethoxyacetimidate (1.12 g, 6.96 mmol) in methanol (10 ml). The mixture was heated at 70 C for 1 h. The mixture was purified by chromatography (Biotage: 100% ethyl acetate) to yield N-(3-chloro-2-fluorobenzyl)-2,2-diethoxyacetimidamide (1.3 g, 4.5 mmol, 65% yield) as a colorless viscous oil. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.23-7.40 (m, 2H), 7.07 (t, J=7.9 Hz, 1H), 4.93 (s, 1H), 4.54 (s, 2H), 3.50-3.74 (m, 4H), 1.18-1.35 (m, 6H). MS (LC/MS) R.T.=1.78; [M+H]+=289.17.

Workup

  1. temperatureThe mixture was heated at 70 C for 1 h
  2. customThe mixture was purified by chromatography (Biotage: 100% ethyl acetate)

Sources & evidence

ORD record
ord-d469ca1d6e8844ea8a62aa87b78bb27d
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

Loading…