m-Chloroperbenzoic acid → HCID 21435659, compound

HRID 2397511Notes

Reaction equation

HRID 2397511 reaction equation
[CH2:1]([S:3][C:4]1[O:5][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)Cl>[CH2:1]([S:3]([C:4]1[O:5][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1)=[O:26])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21435664HCID 21435664, compound

Product 1

HCID 21435659HCID 21435659, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (ice/water) solution of 4.2 g. of 2-ethylthio-4,5-diphenyl-oxazole pre-dissolved in 30 ml. of methylene chloride is added in portions over 5 minutes, 30 g. of m-chloro-peroxybenzoic acid. Examination by TLC after 2 hours indicates the presence of essentially all of the sulfinyl compound (reaction complete). The precipitated m-chloro-benzoic acid is filtered off and the methylene chloride solution is washed successively with a 10 % solution of sodium sulfite and with saturated sodium bicarbonate solution, dried, evaporated in vacuo to dryness, and the residue further dried overnight in vacuo to yield 2-ethylsulfinyl-4,5-diphenyl-oxazole, m.p. 133°-134° C.

Workup

  1. filtrationThe precipitated m-chloro-benzoic acid is filtered off
  2. washthe methylene chloride solution is washed successively with a 10 % solution of sodium sulfite and with saturated sodium bicarbonate solution
  3. customdried
  4. customevaporated in vacuo to dryness
  5. customthe residue further dried overnight in vacuo

Sources & evidence

ORD record
ord-357d9961265145b0bee819dc63f4732c
Source dataset
uspto-grants-1977_05
Patent number
US04022607

Reaction notes

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