Hydrogen Peroxide → HCID 18434120, compound

HRID 2306487Notes

Reaction equation

HRID 2306487 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([C:8]2[CH:23]=[CH:22][C:11]([O:12][CH2:13]/[CH:14]=[CH:15]/[CH2:16][N:17]([CH2:19][C:20]#[N:21])[CH3:18])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-:27].[K+].[K+].OO.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:23]=[CH:22][C:11]([O:12][CH2:13]/[CH:14]=[CH:15]/[CH2:16][N:17]([CH3:18])[CH2:19][C:20]([NH2:21])=[O:27])=[CH:10][CH:9]=2)=[O:7])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 18434117HCID 18434117, compound

Product 1

HCID 18434120HCID 18434120, compoundYield 314.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 0.4 g of (E)-[[4-[4-(4-bromo-benzoyl)-phenoxy]-but-2-enyl]-methyl-amino]-acetonitrile (Ex. 2j) and 0.04 g of potassium carbonate in 3 ml of dimethyl sulphoxide is cooled to 0° C. and treated with 1 ml of 30% hydrogen peroxide solution. The reaction mixture is warmed to room temperature and stirred overnight. For the working up, the mixture is treated with 10 ml of water and the separated crystals are filtered off and washed with water. There is obtained 0.38 g of (E)-2-[[4-[4-(4-bromo-benzoyl)-phenoxy]-but-2-enyl]-methyl-amino]-acetamide, MS: m/e 372 (M+-H2NCO, 1Br).

Workup

  1. temperatureThe reaction mixture is warmed to room temperature
  2. filtrationthe separated crystals are filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-cf36ace969f142e3a71c9eb15ebd333d
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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