Acetyl chloride → Acetamide, N-(4-(diethylamino)phenyl)- (9CI)

HRID 2254536Notes

Reaction equation

C(N(CC)CC)C.Cl.[CH2:9]([N:11]([CH2:19][CH3:20])[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)[CH3:10].[C:21](Cl)(=[O:23])[CH3:22]>ClCCl>[C:21]([NH:18][C:15]1[CH:16]=[CH:17][C:12]([N:11]([CH2:9][CH3:10])[CH2:19][CH3:20])=[CH:13][CH:14]=1)(=[O:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (22.3 g, 30.6 mL, 0.22 mol) was added to a suspension of N,N-diethyl-p-phenylenediamine hydrochloride (20 g, 0.1 mol) in dichloromethane (150 mL) at room temperature. The mixture was cooled to 0° C. and acetyl chloride (7.85 g, 0.1 mol) was added dropwise, with stirring. The mixture was allowed to warm to room temperature, and the precipitate which had formed was removed by filtration. The solid residue was washed with dichloromethane, and the combined dichloromethane solutions were concentrated. The dark oil produced was triturated with hexanes (100 mL) to afford a light brown crystalline solid, which was purified by recrystallization from 50% aqueous ethanol to afford the N-acetyl-4-diethylaminoaniline (16.5 g, 80% yield) as a gray solid. The structure of this compound was confirmed by mass spectroscopy and by 1H NMR spectroscopy.

Workup

temperatureto warm to room temperature
customthe precipitate which had formed
customwas removed by filtration
washThe solid residue was washed with dichloromethane
concentrationthe combined dichloromethane solutions were concentrated
customThe dark oil produced
customwas triturated with hexanes (100 mL)
customto afford a light brown crystalline solid, which
customwas purified by recrystallization from 50% aqueous ethanol

Sources & evidence

ORD record: ord-c3a396a5700c468d823816ad52f686f9
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05236884

Reaction notes

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