4,4'-Thiobis(2-tert-butyl-6-methylphenol) → HCID 178526895, compound

HRID 845325Notes

Reaction equation

HRID 845325 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[C:7]([CH:9](C)[C:10]([OH:12])=[CH2:11])[N:8]=1)([O-:3])=[O:2].C1NC([N+]([O-])=O)=NC=1.C1[O:26][CH:23]1C=C.C(=O)([O-])[O-].[K+].[K+].ClC1C=CC=C(C(OO)=O)C=1.C(C1C=C(SC2C=C(C)C(O)=C(C(C)(C)C)C=2)C=C(C)C=1O)(C)(C)C>C(O)C.ClC(Cl)C>[N+:1]([C:4]1[NH:5][CH:6]=[C:7]([CH2:9][CH:10]([OH:12])[CH:11]2[O:26][CH2:23]2)[N:8]=1)([O-:3])=[O:2]

Participants

9

Reactant 6

HCID 73064,4'-Thiobis(2-tert-butyl-6-methylphenol)HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 13586VinyloxiraneHCID 70297m-Chloroperbenzoic acidHCID 178467748HCID 178467748, compound

Product 1

HCID 178526895HCID 178526895, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 63651,1-DichloroethaneSolvent

Procedure

3-(2-Nitroimidazolyl)-2-hydroxy-1-butene (11.83 gms, m.p. 90°-92° C., prepared by refluxing a mixture of azomycin, 1,3-butadiene monoxide and anydrous potassium carbonate in ethanol for 5 hours) is stirred overnight in dichloroethane with m-chloroperbenzoic acid in the presence of 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide and after stirring the reaction mixture is refluxed for 1 hour. The mixture is washed with saturated sodium carbonate solution and the aqueous phase was extracted with chloroform. The combined dichloroethane and chloroform extracts are concentrated to a small volume and the product is purified by column chromatography, in which silica gel is the stationary phase and a mixture of chloroform (90%) and ethanol (10%) the eluent. The product is crystallized from ethanol as a pale yellow solid of m.p. 134°-136° C. Yield 33%.

Workup

  1. temperatureby refluxing
  2. temperatureis refluxed for 1 hour
  3. washThe mixture is washed with saturated sodium carbonate solution
  4. extractionthe aqueous phase was extracted with chloroform
  5. concentrationThe combined dichloroethane and chloroform extracts are concentrated to a small volume
  6. customthe product is purified by column chromatography, in which silica gel
  7. additiona mixture of chloroform (90%) and ethanol (10%) the eluent
  8. customThe product is crystallized from ethanol as a pale yellow solid of m.p. 134°-136° C

Sources & evidence

ORD record
ord-1088c9c8d1d444d9b3cfa55f6bb81f99
Source dataset
uspto-grants-1988_07
Patent number
US04757148

Reaction notes

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