m-Chloroperbenzoic acid → HCID 10220188, compound

HRID 412055Notes

Reaction equation

HRID 412055 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][N:13]1[CH:18]=[C:17]([S:19][CH3:20])[C:16](=[O:21])[C:15]2[S:22][CH:23]=[CH:24][C:14]1=2>ClCCl>[CH3:12][N:13]1[CH:18]=[C:17]([S:19]([CH3:20])=[O:9])[C:16](=[O:21])[C:15]2[S:22][CH:23]=[CH:24][C:14]1=2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid3×HCID 22250099HCID 22250099, compound

Product 1

HCID 10220188HCID 10220188, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of 3-chloroperbenzoic acid (85%; 1.63 g) in dichloromethane (60 ml) can be added dropwise during 20 minutes to a stirred solution of 4-methyl-6-methylthiothieno[3,2-b]pyrid-7(4H)-one (2.0 g) in dichloromethane (60 ml) at 0° C.-5° C. After 4 hours, more 3-chloroperbenzoic acid (0.15 g) in dichloromethane (10 ml) can be added and the mixture stirred overnight at ambient temperature. More 3-chloroperbenzoic acid (0.15 g) in dichloromethane (10 ml) can be added and the mixture can again be stirred overnight at ambient temperature. The resulting solution can be extracted with saturated aqueous sodium bicarbonate solution (5×150 ml) and saturated aqueous sodium chloride solution (1×150 ml) and the organic phase can be discarded. The aqueous extracts are combined and extracted with dichloromethane (5×100 ml). The organic extracts are combined, dried over anhydrous magnesium sulphate and evaporated to give a solid product. This product can be crystallized from industrial methylated spirit to give the compound 4-methyl-6-methylsulphinylthieno[3,2-b]pyrid-7(4H)-one, m.p. 174° C.-176° C.

Workup

  1. stirringthe mixture can again be stirred overnight at ambient temperature
  2. extractionThe resulting solution can be extracted with saturated aqueous sodium bicarbonate solution (5×150 ml) and saturated aqueous sodium chloride solution (1×150 ml)
  3. extractionextracted with dichloromethane (5×100 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customto give a solid product
  7. customThis product can be crystallized from industrial methylated spirit

Sources & evidence

ORD record
ord-1e3b51ebed7e43bd98974a0806b502f2
Source dataset
uspto-grants-2003_05
Patent number
US06562838B2

Reaction notes

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