m-Chloroperbenzoic acid → HCID 20345013, compound

HRID 2049280Notes

Reaction equation

HRID 2049280 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:23]([O:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])=[CH:22][C:16]2[N:17]=[C:18]([S:20][CH3:21])[NH:19][C:15]=2[CH:14]=1.S(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[C:23]([O:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])=[CH:22][C:16]2[N:17]=[C:18]([S:20]([CH3:21])=[O:9])[NH:19][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 13373882HCID 13373882, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 20345013HCID 20345013, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 19.5 g of 90% pure m-chloroperbenzoic acid in 450 ml of chloroform is added dropwise in the course of 30 minutes to a solution, which has been cooled to 0° to 5° C., of 35 g of 5-chloro-6-(2',4'-dichlorophenoxy)-2-methylthio-benzimidazole in 1,750 ml of chloroform, with stirring. The mixture is stirred for a further 3 hours at 0° to 5° C. and then for 15 hours at room temperature and then is freed from the small amount of precipitate which arises. The filtrate, which still contains residues of m-chloroperbenzoic acid, is treated with sodium bisulphite solution, washed with water, dried over calcium chloride, filtered and concentrated in vacuo. After recrystallising the residue from 500 ml of ethyl acetate, and at the same time clarifying the hot solution with active charcoal, and then drying the white crystals at 50° C., 26 g of 5-chloro-6-(2',4'-dichlorophenoxy)-2-methylsulphinyl-benzimidazole with a melting point of 206°-208° C. are obtained, which corresponds to a yield of 69%.

Workup

  1. stirringThe mixture is stirred for a further 3 hours at 0° to 5° C.
  2. washwashed with water
  3. dry with materialdried over calcium chloride
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customAfter recrystallising the residue from 500 ml of ethyl acetate
  7. customdrying the white crystals at 50° C.

Sources & evidence

ORD record
ord-2741aee8e9d74ff7af14e459169ab909
Source dataset
uspto-grants-1980_04
Patent number
US04197307

Reaction notes

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