Methanol → 2-(4-Methylphenyl)ethanimidamide hydrochloride

HRID 890690Notes

Reaction equation

[Cl-:1].[NH4+:2].C[Al](C)C.[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][C:13]#[N:14])=[CH:10][CH:9]=1.CO>C1(C)C=CC=CC=1.CCCCCC>[ClH:1].[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][C:13]([NH2:2])=[NH:14])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

10.8 g (201 mmol) of ammonium chloride are suspended in 200 ml of dry toluene and the suspension is cooled to 0° C. 100 ml of a 2M solution of trimethylaluminium in hexane are added dropwise and the mixture is stirred at room temperature until the evolution of gas is complete. After addition of 13.2 g (100 mmol) of 4-methylbenzyl cyanide, the reaction mixture is stirred overnight at 80° C. (bath). The cooled reaction mixture is treated with ice-cooling with 35 ml of methanol and then stirred at room temperature for a further 1 h. The solid is then first filtered off with suction, and the filter cake is washed several times with methanol. The filtrate is concentrated, the residue is resuspended in dichloromethane/methanol 10/1 and the insoluble solid is separated off. The filtrate is then again evacuated from the solvent in vacuo.

Workup

stirringthe reaction mixture is stirred overnight at 80° C. (bath)
customThe cooled reaction mixture
additionis treated with ice-
stirringstirred at room temperature for a further 1 h
filtrationThe solid is then first filtered off with suction
washthe filter cake is washed several times with methanol
concentrationThe filtrate is concentrated
customthe insoluble solid is separated off
customThe filtrate is then again evacuated from the solvent in vacuo

Sources & evidence

ORD record: ord-a8c7007e1f3d4d62a64be9bddc9596b7
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06998402B2

Reaction notes

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