Water → HCID 135786536, compound

HRID 1493009Notes

Reaction equation

HRID 1493009 reaction equation
C1C=C([O:7]O)C(C(O)=O)=C(C(O)=O)C=1.[CH3:15][C:16]([C:19]1[CH:24]=[C:23](/[CH:25]=[CH:26]/[C:27]2[S:28][C:29]([S:32][CH3:33])=[N:30][N:31]=2)[CH:22]=[C:21]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:20]=1[OH:38])([CH3:18])[CH3:17].[OH2:39]>CO>[CH3:35][C:34]([C:21]1[CH:22]=[C:23](/[CH:25]=[CH:26]/[C:27]2[S:28][C:29]([S:32]([CH3:33])(=[O:7])=[O:39])=[N:30][N:31]=2)[CH:24]=[C:19]([C:16]([CH3:15])([CH3:17])[CH3:18])[C:20]=1[OH:38])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 962WaterHCID 198097063-Hydroperoxyphthalic acidHCID 135500034HCID 135500034, compound

Product 1

HCID 135786536HCID 135786536, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Monoperoxyphthalic acid, magnesium salt hexahydrate (1.4 g of a 80% pure solid, 0.0056 mole) is added portionwise to a 0° C. solution of (E)-2,6-bis(1,1-dimethylethyl)-4-[2-[5-(methylthio)-1,3,4-thiadiazol-2-yl]ethenyl]-phenol (1.0 g, 0.0028 mole) in methanol (15 ml) and water (7 ml). After the addition is complete the solution is allowed to warm to room temperature and stir for two hours. The mixture is then warmed on a steam bath for 45 minutes before cooling and concentrating in vacuo. The residue is dissolved in ether and washed with saturated aqueous NaHCO3, saturated aqueous NaCl, and dried over MgSO 4. Filtration and concentration in vacuo gives a residue which is purified by flash chromatography (SiO2) using a 15% ethyl acetate/hexane eluent, followed by recrystallization from ethyl acetate/hexane to give 0.22 g (1.1 g theor., 22%) (E)-2,6-bis(1,1-dimethylethyl)-4-[2- [5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl]ethenyl]phenol, mp 235° C.

Workup

  1. additionAfter the addition
  2. temperatureThe mixture is then warmed on a steam bath for 45 minutes
  3. temperaturebefore cooling
  4. concentrationconcentrating in vacuo
  5. dissolutionThe residue is dissolved in ether
  6. washwashed with saturated aqueous NaHCO3, saturated aqueous NaCl
  7. dry with materialdried over MgSO 4
  8. filtrationFiltration and concentration in vacuo
  9. customgives a residue which
  10. customis purified by flash chromatography (SiO2)
  11. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-47752102bebb4180a339b2e1df85b000
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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