m-Chloroperbenzoic acid → HCID 14183130, compound

HRID 845451Notes

Reaction equation

HRID 845451 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]=[C:23]([S:25][NH2:26])[S:22][N:21]=2)=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.ClCCl>COCCOC>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:24]=[C:23]([S:25]([NH2:26])=[O:6])[S:22][N:21]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14183093HCID 14183093, compoundHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 14183130HCID 14183130, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 23.9 g of 85% m-chloroperoxybenzoic acid in 125 ml of 1,2-dimethoxyethane (DME hereafter) was added dropwise over 1 hour to a solution of 14 g of 3-(4-methoxyphenyl)-1,2,4-thiadiazole-5-sulfenamide in 300 ml of DME at -5° (ice/methanol bath). The resulting solution was stirred at room temperature overnight. Concentration gave a solid mass which was stirred for 2 hours with 300 ml of saturated sodium bicarbonate solution, collected, washed with water and dried to give 14.8 g of crude product. Flash chromatography using a step gradient of 12 to 15% ethyl acetate/dichloromethane gave 1.37 g of solid, m.p. 144°-147°.

Workup

  1. concentrationConcentration
  2. customgave a solid mass which
  3. customcollected
  4. washwashed with water
  5. customdried
  6. customto give 14.8 g of crude product

Sources & evidence

ORD record
ord-314cf6c425b6404fa37f5b85e7cb23a6
Source dataset
uspto-grants-1988_07
Patent number
US04758578

Reaction notes

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