Diethyl Ether → HCID 13576506, compound

HRID 638578Notes

Reaction equation

HRID 638578 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]1([S:18][CH2:19][C:20]2[O:24][N:23]=[C:22]([C:25]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)=[O:26])[N:21]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[O-]S([O-])(=S)=O.[Na+].[Na+].CCOCC>C(Cl)Cl>[C:12]1([S:18]([CH2:19][C:20]2[O:24][N:23]=[C:22]([C:25]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)=[O:26])[N:21]=2)=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 20252648HCID 20252648, compound

Product 1

HCID 13576506HCID 13576506, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.14 g of m-chloroperoxybenzoic acid (85%) in 125 ml CH2Cl2 was added dropwise to a solution of 7.5 g of 5-phenylthiomethyl-3-(4-toluoyl)-1,2,4-oxadiazole in 150 ml CH2Cl2 at -70° under N2. The temperature was maintained below -65° during the addition by controlling the addition rate and stirring was continued for 30 minutes after the addition while maintaining the temperature below -65°. The resulting mixture was poured directly into 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 5.3 g (64%) of needles, m.p. 97°-99°.

Workup

  1. temperatureThe temperature was maintained below -65° during the addition
  2. additionafter the addition
  3. temperaturewhile maintaining the temperature below -65°
  4. additionThe resulting mixture was poured directly into a separatory funnel
  5. washThe organics were washed with saturated NaHCO3
  6. dry with materialdried over MgSO4
  7. concentrationConcentration
  8. customgave an oil which
  9. customRecrystallization from acetone/hexane

Sources & evidence

ORD record
ord-1c275659c7b54cf2bc6b5ee45ecc28ce
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

Loading…