Water → N-methyl-2-(2-bromomethylphenyl)-2-methoxyiminoacetamide

HRID 1585815Notes

Reaction equation

[C:1]([Br:5])(Br)(Br)Br.[CH3:6][NH:7][C:8](=[O:21])[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1CO)=[N:10][O:11][CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[CH3:6][NH:7][C:8](=[O:21])[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:1][Br:5])=[N:10][O:11][CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Carbon tetrabromide (0.33 g) was added to a solution of N-methyl-2-(2-hydroxymethylphenyl)-2-methoxyiminoacetamide (0.11 g) and triphenylphosphine (0.26 g) in tetrahydrofuran (10 ml) at 0° C. The reaction mixture was stirred at 0° C. for 11/2 hours and then at room temperature for 1 hour. The reaction mixture was then poured into water and extracted three times with ethyl acetate. The combined extracts were washed with brine and dried over magnesium sulphate. The solution was then concentrated under reduced pressure to leave a gum. Column chromatography (eluting with diethyl ether on silica gel) gave the N-methyl-2-(2-bromomethylphenyl)-2-methoxyiminoacetamide as a gum (80 mg, 57%). 1H NMR (CDCl3) δ 2.95(d,3H), 4.0(s,3H), 4.35(s,2H), 6.8(brs,1H), 7.1-7.5(m,4H) ppm.

Workup

waitat room temperature for 1 hour
extractionextracted three times with ethyl acetate
washThe combined extracts were washed with brine
dry with materialdried over magnesium sulphate
concentrationThe solution was then concentrated under reduced pressure
customto leave a gum
washColumn chromatography (eluting with diethyl ether on silica gel)

Sources & evidence

ORD record: ord-07eecb609eca4c209dea6d902439d0f7
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05939563

Reaction notes

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