Hydrogen Peroxide → 1-(4-Bromophenyl)-3,3-dimethoxycyclobutanecarboxamide

HRID 1509315ノート

反応式

HRID 1509315 の反応式
OO.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:18]#[N:19])[CH2:13][C:12]([O:16][CH3:17])([O:14][CH3:15])[CH2:11]2)=[CH:6][CH:5]=1.C(=O)([O-])[O-:21].[K+].[K+].O>CS(C)=O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:18]([NH2:19])=[O:21])[CH2:13][C:12]([O:14][CH3:15])([O:16][CH3:17])[CH2:11]2)=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 594871351-(4-Bromophenyl)-3,3-dimethoxycyclobutanecarbonitrile

生成物 1

HCID 672542661-(4-Bromophenyl)-3,3-dimethoxycyclobutanecarboxamide収率 488.5%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Hydrogen peroxide (2.05 ml, 20.07 mmol) was added over 2 h to a stirred mixture of 1-(4-bromophenyl)-3,3-dimethoxycyclobutanecarbonitrile (3.18 g, 10.74 mmol) and Potassium carbonate (0.297 g, 2.15 mmol) in DMSO (11 ml) at 40 degree under a nitrogen atmosphere. After the addition, the reaction mixture was heated to 80 degree for 3 h. The reaction mixture was allowed to cool down to room temperature and water (30 ml) was added. The reaction mixture was extracted with ethyl acetate (3×20 ml). The combined organic phase was washed with water (2×30 ml), brine (30 ml), concentrated to give light yellow oil (3.3 g). 1H NMR (500 MHz, CDCl3) 7.40 (d, 2H), 7.11 (d, 2H), 5.89 (br, 1H), 5.58 (br, 1H), 3.12 (s, 3H), 3.02 (s, 3H), 2.97 (d, 2H), 2.52 (d, 2H).

後処理

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated to 80 degree for 3 h
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×20 ml)
  4. washThe combined organic phase was washed with water (2×30 ml), brine (30 ml)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-a8d906d6df8446caa0da94adeb381cd2
出典データセット
uspto-grants-2015_12
特許番号
US09221838B2

反応ノート

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