m-Chloroperbenzoic acid → HCID 14183131, compound

HRID 2351350Notes

Reaction equation

HRID 2351350 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[N:23]=[C:22]([S:24][NH2:25])[S:21][N:20]=1.C(=O)(O)[O-].[Na+]>COCCOC>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[N:23]=[C:22]([S:24]([NH2:25])=[O:6])[S:21][N:20]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14183124HCID 14183124, compound

Product 1

HCID 14183131HCID 14183131, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 3.45 g of 85% m-chloroperoxybenzoic acid in 100 ml of DME was added to a solution of 4 g of 3-(2-chlorophenyl)-1,2,4-thiadiazole-5-sulfenamide in 150 ml of DME at -70° C. over an hour. The resulting solution was stirred for 2 hours at -70° and thereafter warmed to room temperature. Concentration gave a solid which was stirred with 100 ml of sodium bicarbonate solution overnight. The solid was collected and the filtrate was extracted with ethyl acetate/dichloromethane. Concentration gave 0.7 g of solid which was recrystallized in benzene to give 0.52 g of solid, m.p. 130°-131°.

Workup

  1. concentrationConcentration
  2. customgave a solid which
  3. customThe solid was collected
  4. extractionthe filtrate was extracted with ethyl acetate/dichloromethane
  5. concentrationConcentration

Sources & evidence

ORD record
ord-1b0031bbd8d2423eb020a9925c24ba83
Source dataset
uspto-grants-1989_10
Patent number
US04873239

Reaction notes

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