Triethylamine → 4-bromo-N-methoxy-N,2-dimethylbenzamide

HRID 1671354Notes

Reaction equation

C(N(CC)CC)C.Cl.[CH3:9][NH:10][O:11][CH3:12].[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[C:16]([CH3:23])[CH:15]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([N:10]([O:11][CH3:12])[CH3:9])=[O:19])=[C:16]([CH3:23])[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (1.3 ml, 10.04 mmol) is added to a stirred suspension of N,O-dimethylhydroxylamine hydrochloride (0.45 g, 4.6 mmol) in toluene (15 ml). After 30 minutes at RT the solution is cooled to 0° C. and a solution of 4-bromo-2-methylbenzoyl chloride (0.977 g, 4.81 mmol) in toluene (5 ml) is slowly added. The reaction is stirred at RT for 2 h at 0° C. and then diluted with ethyl acetate. The mixture is washed with 0.1M aq. HCl solution followed by brine. The organic extract is separated, dried over (MgSO4) and concentrated in vacuo to afford a colourless oil. Purification by chromatography on silica, eluting with ethyl acetate:iso-hexane (1:1) yields the title product as a colourless oil. MS m/z 258.0 [M+H]+1H NMR (400 MHz, CDCl3) δ 2.32 (3H, s), 3.0 (3H, br s), 3.50 (3H, br s), 7.15 (1H, d), 7.35 (1H, d), 7.37 (1H, s).

Workup

washThe mixture is washed with 0.1M aq. HCl solution
extractionThe organic extract
customis separated
dry with materialdried over (MgSO4)
concentrationconcentrated in vacuo
customto afford a colourless oil
customPurification by chromatography on silica
washeluting with ethyl acetate:iso-hexane (1:1)

Sources & evidence

ORD record: ord-7e3aef7972c043af92b81804f75f2be5
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994203B2

Reaction notes

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