Water → HCID 13922896, compound

HRID 979592Notes

Reaction equation

HRID 979592 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][S:5][CH2:6][C:7]1[CH:19]=[CH:18][C:10]2[S:11][C:12]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:13][C:9]=2[CH:8]=1.S([O-])(O[O-])(=O)=[O:22].[K+].[K+].OOS([O-])=O.[K+].C([O-])(O)=O.[Na+].[OH2:40]>>[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][S:5]([CH2:6][C:7]1[CH:19]=[CH:18][C:10]2[S:11][C:12]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:13][C:9]=2[CH:8]=1)(=[O:22])=[O:40]

Participants

6

Reactant 5

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 13922894HCID 13922894, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 13922896HCID 13922896, compoundYield 34%

Procedure

To a solution of 5-[2-(dimethylamino)ethylthiomethyl]-2-sulfamoylbenzo[b]thiophene (2.34 g, 0.0064 mol) in 20 ml of water at 40-45° C. was added potassium peroxymonosulfate, "oxone", (5.93 g, 0.0096 mol). The mixture was stirred at room temperature over night and heated on the steam bath for 2 1/2 hours. The mixture was cooled and basified with NaHCO3. Filtration gave 2.5 g of crude product. Purification by silica gel chromatography eluting with 10% (V/V) methanol/CHCl3 gave 0.78 g of pale pink solid, m.p. 185.5-187° C., dec. (Yield 34%).

Workup

  1. temperatureheated on the steam bath for 2 1/2 hours
  2. temperatureThe mixture was cooled
  3. filtrationFiltration
  4. customgave 2.5 g of crude product
  5. customPurification by silica gel chromatography
  6. washeluting with 10% (V/V) methanol/CHCl3

Sources & evidence

ORD record
ord-1f43a20550664c1b9e614336c2bc39fb
Source dataset
uspto-grants-1987_05
Patent number
US04668697

Reaction notes

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