m-Chloroperbenzoic acid → HCID 18374274, compound

HRID 2300028Notes

Reaction equation

HRID 2300028 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:14][C:15]1[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[C:18]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:17][CH:16]=1)[CH3:13]>C(Cl)Cl>[CH2:12]([S:14]([C:15]1[N:20]=[C:19]([C:21]([F:24])([F:22])[F:23])[C:18]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:17][CH:16]=1)=[O:9])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18374282HCID 18374282, compound

Product 1

HCID 18374274HCID 18374274, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of nitrogen and with stirring and cooling, a solution of 2.5 g of m-chloroperbenzoic acid in 40 ml of methylene chloride is added dropwise at a temperature of −20° C. to a solution of 2.8 g of ethyl 6-ethylthio-2-trifluoromethylpyridin-3-ylcarboxylate, which had been charged initially, and the mixture is stirred at a temperature of +5° C. for 20 hours. The mixture is then evaporated gently and purified over silica gel (hexanelethyl acetate 7:3). This gives 2.48 g (84%) of 6-ethylsulfinyl-2-trifluoromethylpyridin-3-yl-ethyl ester. 1H NMR (CDCl3, ppm): 8.38 (d, 1H); 8.30 (d, 1H); 4.45 (q, 2H); 3.26-3.00 (m, 2H); 1.43 (t, 3H); 1.26 (t, 3H).

Workup

  1. temperaturecooling
  2. additionhad been charged initially
  3. stirringthe mixture is stirred at a temperature of +5° C. for 20 hours
  4. customThe mixture is then evaporated gently
  5. custompurified over silica gel (hexanelethyl acetate 7:3)

Sources & evidence

ORD record
ord-9a361a32817c4813897686b8a9854fc7
Source dataset
uspto-grants-2002_12
Patent number
US06498125B2

Reaction notes

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