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

HRID 1509315Notes

Reaction equation

HRID 1509315 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a8d906d6df8446caa0da94adeb381cd2
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

Loading…