Chloroform → HCID 21251011, compound

HRID 1531838Notes

Reaction equation

HRID 1531838 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[C:7]1([N:13]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[N:15]=[C:14]2SC)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:24](Cl)(Cl)Cl>>[C:7]1([N:13]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[N:15]=[C:14]2[S:3]([CH3:24])(=[O:5])=[O:2])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 6212Chloroform2×HCID 21250999HCID 21250999, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 21251011HCID 21251011, compoundYield 62%

Conditions

Temperature
0 °C

Procedure

3.8 g of previously moistened alumina, 7.07 g (11.5 mmol) of oxone and 10 ml of chloroform are vigorously stirred. A solution of 0.9 g (3.7 mmol) of 1-phenyl-2-methylthio-4,5,6,7-tetrahydro-1H-benzimidazole, solubilized in 10 ml of chloroform, is added to this medium and then the stirring is continued while heating under reflux for 2 hours. The mixture is cooled to 0° C. and then filtered, the solid is rinsed with 10 ml of chloroform and 10 ml of a 9/1 THF/CH3OH mixture. The filtrate is concentrated under reduced pressure and then purified on a silica column with the aid of a 99/1 then 98/2 dichloromethane/methanol mixture. 0.65 g of product is obtained. Yield=62%.

Workup

  1. additionis added to this medium
  2. temperaturewhile heating
  3. temperatureunder reflux for 2 hours
  4. filtrationfiltered
  5. washthe solid is rinsed with 10 ml of chloroform and 10 ml of a 9/1 THF/CH3OH mixture
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. custompurified on a silica column with the aid of a 99/1

Sources & evidence

ORD record
ord-a92ad32764fd423ebde7a4596d235764
Source dataset
uspto-grants-2001_03
Patent number
US06200991B1

Reaction notes

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