Diethyl Ether → HCID 13576504, compound

HRID 638576Notes

Reaction equation

HRID 638576 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([C:20]1[N:24]=[C:23]([CH2:25][S:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:22][N:21]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O-]S([O-])(=S)=O.[Na+].[Na+].CCOCC>C(Cl)Cl>[C:12]([C:20]1[N:24]=[C:23]([CH2:25][S:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:6])[O:22][N:21]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 20252656HCID 20252656, compound

Product 1

HCID 13576504HCID 13576504, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.5 g of m-chloroperoxybenzoic acid (85%) in 125 ml of CH2Cl2 was added dropwise at -70° C. under N2 to a solution of 7.5 g of 3-benzoyl-5-phenylthiomethyl-1,2,4-oxadiazole in 150 ml of CH2Cl2. The temperature of the reaction was maintained below -65° by controlling the rate of addition. After stirring further for 30 minutes, the reaction mixture was added directly to a separatory funnel containing 250 ml of 10% Na2S2O3 and 500 ml of Et2O. The organics were washed with saturated NaHCO3 and dried over MgSO4. Concentration gave an oil which solidified on standing. Recrystallization from acetone/hexane gave 3.7 g (44%) of needles, m.p. 79°-81°.

Workup

  1. temperatureThe temperature of the reaction was maintained below -65°
  2. additionthe rate of addition
  3. additionthe reaction mixture was added directly to a separatory funnel
  4. washThe organics were washed with saturated NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationConcentration
  7. customgave an oil which
  8. customRecrystallization from acetone/hexane

Sources & evidence

ORD record
ord-8a74f14edc46471e855f55757581c447
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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