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

HRID 1509315노트

반응식

HRID 1509315 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 672542661-(4-Bromophenyl)-3,3-dimethoxycyclobutanecarboxamide수율 488.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a8d906d6df8446caa0da94adeb381cd2
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221838B2

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