m-Chloroperbenzoic acid → HCID 69290058, compound

HRID 750977Notes

Reaction equation

HRID 750977 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[S:6][CH:7]=1.ClC1C=C(C(OO)=[O:29])C=CC=1>ClCCl>[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([S:16]([C:17]([F:20])([F:19])[F:18])=[O:29])=[CH:14][CH:15]=2)[S:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69291784HCID 69291784, compound

Product 1

HCID 69290058HCID 69290058, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.50 g (1.5 mmol) 4-chloromethyl-2-[2-(4-trifluoromethylsulfanyl-phenyl)-vinyl]-thiazole in 20 ml dichloromethane was stirred with 0.31 g (1.8 mmol) 3-chloro-benzenecarboperoxoic acid at room temperature for 2 days. The solution was washed with diluted sodium hydroxide, dried, evaporated and purified on silica. Elution with ethyl acetate/heptane 1:6 yielded 270 mg (52%) 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-thiazole as off-white solid, melting at 98-99° C.

Workup

  1. washThe solution was washed with diluted sodium hydroxide
  2. customdried
  3. customevaporated
  4. custompurified on silica
  5. washElution with ethyl acetate/heptane 1:6

Sources & evidence

ORD record
ord-36a579f151c642b798a57fe6b2aa47e7
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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