m-Chloroperbenzoic acid → 2-(methylsulphinyl)-1H-naphth[2,3-d]imidazole

HRID 1413109Notes

Reaction equation

HRID 1413109 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][S:13][C:14]1[NH:18][C:17]2[CH:19]=[C:20]3[C:25](=[CH:26][C:16]=2[N:15]=1)[CH:24]=[CH:23][CH:22]=[CH:21]3>C(Cl)Cl>[CH3:12][S:13]([C:14]1[NH:15][C:16]2[CH:26]=[C:25]3[C:20](=[CH:19][C:17]=2[N:18]=1)[CH:21]=[CH:22][CH:23]=[CH:24]3)=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 128720792-(methylthio)-1H-naphtho[2,3-d]imidazole

Product 1

HCID 202935532-(methylsulphinyl)-1H-naphth[2,3-d]imidazoleYield 49.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.2 g of m-chloroperbenzoic acid in 100 ml of methylenechloride was added dropwise at 0°-5° to 4.3 g of 2-(methylthio)-1H-naphth[2,3-d]imidazole in 500 ml of methylenechloride. The reaction solution was stirred for 90 minutes at 0°, washed twice with aqueous potassium bicarbonate solution and once with saturated sodium chloride solution, dried over magnesium sulphate, and concentrated by evaporation on a rotary evaporator. Crystallisation from acetonitrile gave 2.3 g of 2-(methylsulphinyl)-1H-naphth[2,3-d]imidazole having a m.p. of 194°.

Workup

  1. washwashed twice with aqueous potassium bicarbonate solution and once with saturated sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated by evaporation on a rotary evaporator
  4. customCrystallisation from acetonitrile

Sources & evidence

ORD record
ord-3da79aa227f84e6b893dc1ba5d1fc0b4
Source dataset
uspto-grants-1981_02
Patent number
US04248880

Reaction notes

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