Diethyl Ether → HCID 13576505, compound

HRID 638577Notes

Reaction equation

HRID 638577 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:33]=[CH:32][C:16]([C:17]([C:19]2[N:23]=[C:22]([CH2:24][S:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:21][N:20]=2)=[O:18])=[CH:15][CH:14]=1.[O-]S([O-])(=S)=O.[Na+].[Na+].CCOCC>C(Cl)Cl>[Cl:12][C:13]1[CH:33]=[CH:32][C:16]([C:17]([C:19]2[N:23]=[C:22]([CH2:24][S:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:6])[O:21][N:20]=2)=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 20252652HCID 20252652, compound

Product 1

HCID 13576505HCID 13576505, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.8 g of m-chloroperoxybenzoic acid (85%) in 150 ml of CH2Cl2 was added dropwise at -70° under N2 to a solution of 9.0 g of 3-(4-chlorobenzoyl)-5-phenylthiomethyl-1,2,4-oxadiazole in 200 ml of CH2Cl2. The reaction temperature was maintained below -65° by controlling the rate of addition. After stirring further for 30 minutes, the reaction mixture was poured directly into a separatory funnel containing 300 ml of 10% Na2S2O3 and 600 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 6.7 g (67%) of needles, m.p. 93°-95°.

Workup

  1. temperatureThe reaction temperature was maintained below -65°
  2. additionthe rate of addition
  3. additionthe reaction mixture was poured directly into 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-38c1e382d34f4e0e87bf6cae7916d7fc
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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