Benzenemethanamine, 3,4-dichloro- → N-(3,4-dichlorobenzyl)-2,2-diethoxyacetimidamide

HRID 250118Notes

Reaction equation

HRID 250118 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][NH2:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[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[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[CH2:9][NH:10][C:15](=[NH:18])[CH:14]([O:19][CH2:20][CH3:21])[O:13][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 17874536Methyl 2,2-diethoxyethanecarboximidate

Product 1

HCID 178471675N-(3,4-dichlorobenzyl)-2,2-diethoxyacetimidamideYield 80.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

(3,4-Dichlorophenyl)methanamine (2 g, 11.4 mmol) was added to a solution of methyl 2,2-diethoxyacetimidate (2.04 g, 12.6 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). The desired fractions were concentrated to yield N-(3,4-dichlorobenzyl)-2,2-diethoxyacetimidamide (2.8 g, 9.2 mmol, 72.7% yield) as a colorless viscous oil. 1H NMR (500 MHz, CDCl3) δ ppm 7.45 (m, 1 H), 7.40 (m, 1 H), 7.19 (dd, J=8.09, 1.98 Hz, 1 H), 4.94 (s, 1 H), 4.43 (s, 2 H), 3.47-3.77 (m, 4 H), 1.41-1.79 (m, 6 H). LC/MS RT=2.15; [M+H]+=305.1.

Workup

  1. customThe mixture was purified by chromatography (Biotage: 100% ethyl acetate)
  2. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-459da382834f4732ba3dbd48e3d26805
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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