2,4-Dichlorobenzylamine → N-(2,4-dichlorobenzyl)-2,2-diethoxyacetimidamide

HRID 1875980Notes

Reaction equation

HRID 1875980 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH2:10].[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:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[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 14852,4-DichlorobenzylamineHCID 17874536Methyl 2,2-diethoxyethanecarboximidate

Product 1

HCID 178471674N-(2,4-dichlorobenzyl)-2,2-diethoxyacetimidamideYield 80.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

(2,4-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-(2,4-dichlorobenzyl)-2,2-diethoxyacetimidamide (2.8 g, 9.2 mmol, 72.7% yield) as a colorless viscous oil. 1H NMR (500 MHz, DMSO-D6) δ ppm 7.27-7.70 (m, 3H), 4.77 (s, 1H), 4.14-4.35 (m, 2H), 3.45-3.68 (m, 4H), 1.09-1.29 (m, 6H). LC/MS RT=2.03; [M+H]+=304.9.

Workup

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

Sources & evidence

ORD record
ord-02c5647ff8d0434a84dbfe0b097a7287
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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