m-Chloroperbenzoic acid → 5-Acetyl-2-(methanesulfinyl)thiophene-3-carbonitrile

HRID 982011Notes

Reaction equation

HRID 982011 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][S:13][C:14]1[S:15][C:16]([C:21](=[O:23])[CH3:22])=[CH:17][C:18]=1[C:19]#[N:20].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH3:12][S:13]([C:14]1[S:15][C:16]([C:21](=[O:23])[CH3:22])=[CH:17][C:18]=1[C:19]#[N:20])=[O:9]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 20069010HCID 20069010, compound

Product 1

HCID 200689985-Acetyl-2-(methanesulfinyl)thiophene-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

5.0 g of 83% m-chloroperbenzoic acid are gradually added while stirring at a temperature of 0°-5° C. in 45 minutes to a solution of 5.0 g of 2-methylthio-3-cyano-5-acetylthiophene in 500 ml of methylene chloride. After stirring for another 30 minutes at 5° C., a saturated solution of sodium bicarbonate in approximately 50 ml of water is added; the reaction mixture is then stirred for 60 minutes. The organic layer is separated, washed with water and dried. After distilling off the solvent, the desired product is obtained in a yield of 4.6 g; melting-point 150° C.

Workup

  1. stirringthe reaction mixture is then stirred for 60 minutes
  2. customThe organic layer is separated
  3. washwashed with water
  4. customdried
  5. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-dfdb45ae2dc94ab197157b2c2f99f046
Source dataset
uspto-grants-1991_02
Patent number
US04994485

Reaction notes

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