Dimethyl Sulfoxide → HCID 90313711, compound

HRID 1524134Notes

Reaction equation

HRID 1524134 reaction equation
OO.[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([C:13]1([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11].C([O-])([O-])=[O:21].[K+].[K+].CS(C)=O>O>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([C:13]1([C:18]([NH2:19])=[O:21])[CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 43519349HCID 43519349, compound

Product 1

HCID 90313711HCID 90313711, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 30% H2O2 solution (1.6 mL) was added drop-wise at rt to a mixture of 1-(2-bromophenylsulfonyl)cyclopentanecarbonitrile (1.6 g, 5.1 mmol), K2CO3 (2.1 g, 15 mmol), and DMSO (5 mL). The mixture was stirred for 30 min before diluting with water (40 mL) and isolating the precipitate via vacuum filtration. The precipitate was washed with water and air-dried to give the title compound (1.5 g, 89%). MS (ESI): mass calcd. for C12H19NO3S, 330.99; m/z found, 331.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 7.99-7.95 (m, 1H), 7.89-7.84 (m, 1H), 7.64-7.51 (m, 4H), 2.41-2.25 (m, 4H), 1.78-1.66 (m, 2H), 1.58-1.45 (m, 2H).

Workup

  1. customisolating the precipitate
  2. filtrationvia vacuum filtration
  3. washThe precipitate was washed with water
  4. customair-dried

Sources & evidence

ORD record
ord-c116aa053b4246f8be8d6b576fdd04db
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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