m-ethylphenyl-N-methylcyanamide → N,N'-di-(m-ethylphenyl)-N-methylguanidine

HRID 257663

Reaction equation

HRID 257663 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].Cl.[CH2:14]([C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19])[CH3:15]>ClCCl>[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:12])[C:10]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:16]([CH2:14][CH3:15])[CH:17]=2)=[NH:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 10103434m-ethylphenyl-N-methylcyanamideHCID 21191493m-Ethylaniline hydrochloride

Product 1

HCID 178436394N,N'-di-(m-ethylphenyl)-N-methylguanidineYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(m-ethylphenyl)-N-methylcyanamide (640 mg, 4 mmol) and m-ethylaniline hydrochloride (630 mg, 4 mmol) was placed in a preheated oil bath at 160° C. for 2.5 hours and then allowed to cool to room temperature. The resulting solid was taken up in dichloromethane and washed with 10% NAOH solution. The organic layer concentrated and the residue was flash chromatographed on SiO2 to give N,N'-di-(m-ethylphenyl)-N-methylguanidine (630 mg, 56%) as a colorless liquid:

Workup

  1. washwashed with 10% NAOH solution
  2. concentrationThe organic layer concentrated
  3. customchromatographed on SiO2

Sources & evidence

ORD record
ord-23f092a4d4fd419bad7b04c2d1e3873d
Source dataset
uspto-grants-1993_11
Patent number
US05262568

Linked notes

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