m-Chloroperbenzoic acid → HCID 67946158, compound

HRID 845450Notes

Reaction equation

HRID 845450 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][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-:27].[Na+]>COCCOC>[OH2:6].[CH3:12][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:27])[S:21][N:20]=1.[CH3:12][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 14183121HCID 14183121, compound

Product 1

HCID 67946158HCID 67946158, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 3.86 g of 85% m-chloroperoxybenzoic acid (MCPBA) in 100 ml of 1,2-dimethoxyethane (DME) was added to a solution of 4 g of 3-(2-methylphenyl)-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 at room temperature overnight. Concentration gave a solid which was stirred with 100 ml of sodium bicarbonate solution for 2 hours, collected, washed with water and dried. Recrystallization from cyclohexane/toluene (2:1) gave 2.2 g of solid, m.p. 110°-112°.

Workup

  1. customat room temperature
  2. customovernight
  3. concentrationConcentration
  4. customgave a solid which
  5. customcollected
  6. washwashed with water
  7. customdried
  8. customRecrystallization from cyclohexane/toluene (2:1)

Sources & evidence

ORD record
ord-31ece380b6e84ab594eb3c42c2a5a5a5
Source dataset
uspto-grants-1988_07
Patent number
US04758578

Reaction notes

Loading…