Triethylamine → (+/-)-N-[2,6-bis(1-Methylethyl)phenyl]-alpha-bromobenzeneacetamide

HRID 465644Notes

Reaction equation

[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].[CH:12]([C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[C:16]=1[NH2:17])([CH3:14])[CH3:13].C(N(CC)CC)C>C(OCC)(=O)C.ClCCl>[CH3:24][CH:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:15]([CH:12]([CH3:14])[CH3:13])[C:16]=1[NH:17][C:3](=[O:4])[CH:2]([Br:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:23]

Participants

Conditions

Temperature: 25 °C

Procedure

The α-bromophenylacetylchloride (21.0 g, 89.7 mmol) was added slowly via pipet to a cooled (0° C.) solution of 2,6-diisopropylaniline (15.9 g, 89.7 mmol) and triethylamine (12.5 mL, 89.7 mmol) in ethyl acetate (1600 mL). The resulting slurry was warmed (25° C.) then stirred (1 hour). The resulting mixture was diluted with ethyl acetate (1000 mL) and dichloro methane (500 mL), then washed with water (1000 mL), with 0.5N aqueous HCl (2×1000 mL), with saturated aqueous sodium bicarbonate (1×600 mL), with brine (1×600 mL), then dried (MgSO4) and concentrated to a solid. The solid was recrystallized from ethyl acetate to yield 27.2 g (81.0%) of (±)-N-[2,6-bis(1-Methylethyl)phenyl]-α-bromobenzeneacetamide as a white solid, mp 207°-209.5° C.

Workup

washwashed with water (1000 mL), with 0.5N aqueous HCl (2×1000 mL), with saturated aqueous sodium bicarbonate (1×600 mL), with brine (1×600 mL)
dry with materialdried (MgSO4)
concentrationconcentrated to a solid
customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-8debb7ff68434656acd98d2d4aca9b04
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05153226

Reaction notes

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