Sodium Methoxide → HCID 178440703, compound

HRID 466056Notes

Reaction equation

HRID 466056 reaction equation
C[O-:2].[Na+].[CH3:4][C:5]([C:8]1[C:9](O)=[C:10]([CH:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=1)[C:11]([NH:13][NH:14][C:15](=[S:17])[NH2:16])=O)([CH3:7])[CH3:6]>CO>[CH3:4][C:5]([C:8]1[CH:9]=[C:10]([C:11]2[NH:16][C:15](=[S:17])[NH:14][N:13]=2)[CH:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:20]=1[OH:2])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18949850HCID 18949850, compound

Product 1

HCID 178440703HCID 178440703, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (2.2 g, 0.041 mole) is added to a solution of 2-[3,5-bis(1,1-dimethylethyl)-hydroxybenzoyl]-hydrazinecarbothioamide (4.0 g, 0.0124 mole) in methanol (50 ml). The resulting mixture is stirred at reflux under an atmosphere of nitrogen for 24 hours. The solution is cooled and concentrated in vacuo. The residue is dissolved in water (25 ml) and washed with ether (2×20 ml). The aqueous layer is acidified with cold aqueous 2M HCl (25 ml) and the product extracted out with a 1:1 mixture of ethyl acetate/ether (2×30 ml). The combined organic extracts are washed with saturated aqueous NaCl and dried over MgSO4. Filtration and concentration gives a residue which is purified by flash chromatography (SiO2, 30% ethyl acetate/hexane eluent). The solid product is recrystallized from ethyl acetate/hexane to give 2.3 g of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione. (3.8 g theor., 61%): mp 271 ° C.

Workup

  1. temperatureat reflux under an atmosphere of nitrogen for 24 hours
  2. temperatureThe solution is cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in water (25 ml)
  5. washwashed with ether (2×20 ml)
  6. extractionthe product extracted out with a 1:1 mixture of ethyl acetate/ether (2×30 ml)
  7. washThe combined organic extracts are washed with saturated aqueous NaCl
  8. dry with materialdried over MgSO4
  9. filtrationFiltration and concentration
  10. customgives a residue which
  11. customis purified by flash chromatography (SiO2, 30% ethyl acetate/hexane eluent)
  12. customThe solid product is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9013390548124e7e8c6043bf71ac9264
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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