Thiazole → HCID 12474103, compound

HRID 2397508Notes

Reaction equation

HRID 2397508 reaction equation
[CH3:1][S:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:19].S1C=CN=C1>C(Cl)Cl>[CH3:1][S:2]([C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1)=[O:19]

Participants

5

Reactant 3

HCID 9256ThiazoleHCID 70297m-Chloroperbenzoic acidHCID 12457584HCID 12457584, compound

Product 1

HCID 12474103HCID 12474103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (ice/water) solution of 8.9 g. of 2-methylthio-4-phenyl-thiazole pre-dissolved in 90 ml. of methylene chloride is added in portions over 5 minutes, 8.7 g. of m-chloro-peroxybenzoic acid. Examination by TLC after 90 minutes indicates the presence of essentially all of the sulfinyl compound (reaction complete) with a faint trace of sulfone and an even fainter trace of remaining thiazole starting material. 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-methylsulfinyl-4-phenyl-thiazole, m.p. 104°-105° 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-9c66ff25964e47b3bd061fbe9d99ec80
Source dataset
uspto-grants-1977_05
Patent number
US04022607

Reaction notes

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