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

HRID 1956023ノート

反応式

HRID 1956023 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

生成物 1

HCID 53790204N-methyl-2-(2-bromomethylphenyl)-2-methoxyiminoacetamide収率 57%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b9e1a004cc534dc8b485e1481662ee71
出典データセット
uspto-grants-1998_07
特許番号
US05777162

反応ノート

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