Water → HCID 14289420, compound

HRID 1651539Notes

Reaction equation

HRID 1651539 reaction equation
[C:1]([NH:9][C:10](=[NH:18])[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCl)(C)(C)C.[OH-].[Na+].O>C(O)C>[O:11]([C:10]1[N:9]=[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:8][N:18]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 521297Tert-Butyl hypochloriteHCID 145809022HCID 145809022, compound

Product 1

HCID 14289420HCID 14289420, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

N-benzoyl-O-phenylisourea (0.8 g) was dissolved in ethanol (40 ml), and t-butylhypochlorite (0.36 g) was added at 0° to 5° C. After one hour, 2 molar aqueous sodium hydroxide (2 ml) was added and the mixture was stirred for 2 hours at ambient temperature (20° C.). The reaction mixture was poured into an equal volume of water and extracted with dichloromethane (100 ml). The separated organic layer was evaporated under reduced pressure and the residue was purified by chromatography over silica gel using dichloromethane as eluant to give 3-phenoxy-5-phenyl-1,2,4-oxadiazole (0.4 g, 57%), m.p. 62° C.

Workup

  1. extractionextracted with dichloromethane (100 ml)
  2. customThe separated organic layer was evaporated under reduced pressure
  3. customthe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-3a2adb6703ea4eee80ba828bfb17ff0c
Source dataset
uspto-grants-1990_05
Patent number
US04929628

Reaction notes

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