m-Chloroperbenzoic acid → HCID 178493618, compound

HRID 845410Notes

Reaction equation

HRID 845410 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][O:13][C:14]1[CH:19]=[C:18]([S:20][CH3:21])[CH:17]=[CH:16][C:15]=1[C:22]1[NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][C:25]=2[N:30]=1>C(Cl)(Cl)Cl>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([S:20]([CH3:21])=[O:6])[CH:17]=[CH:16][C:15]=1[C:22]1[NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][C:25]=2[N:30]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178493617HCID 178493617, compound

Product 1

HCID 178493618HCID 178493618, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 911 mg. (4.22 mmoles) of m-chloroperoxybenzoic acid in 50 ml. of chloroform was added in a dropwise fashion to a solution of 1.15 gm. (4.23 mmoles) 2-(2-methoxy-4-methylmercaptophenyl)imidazo[4,5-c]pyridine in 150 ml. of chloroform at 0° C. The reaction was stirred overnight at 0° C., washed with dilute aqueous sodium bicarbonate, and the solvent removed in vacuo. The residue was flash chromatographed over silica gel using dichloromethane/methanol (9:1) affording 620 mg. (51% yield) of the title product, m.p. about 143°-146° C. (decomposition).

Workup

  1. customat 0° C
  2. washwashed with dilute aqueous sodium bicarbonate
  3. customthe solvent removed in vacuo
  4. customchromatographed over silica gel
  5. customaffording 620 mg

Sources & evidence

ORD record
ord-949adfb7cc424843ba53064d437f6e32
Source dataset
uspto-grants-1988_07
Patent number
US04758574

Reaction notes

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