Sodium Perborate → 2,6-Bis(1,1-dimethylethyl)-4-[[5-(methylsulfinyl)-1,3,4-thiadiazol-2-yl]thio]-phenol

HRID 1029542Notes

Reaction equation

HRID 1029542 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([S:11][C:12]2[S:13][C:14]([S:17][CH3:18])=[N:15][N:16]=2)[CH:8]=[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:6]=1[OH:23])([CH3:4])[CH3:3].B(O[O-])=[O:25].[Na+]>C(O)(=O)C.CCOCC>[CH3:20][C:19]([C:7]1[CH:8]=[C:9]([S:11][C:12]2[S:13][C:14]([S:17]([CH3:18])=[O:25])=[N:15][N:16]=2)[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:6]=1[OH:23])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 517072Sodium PerborateHCID 199006582,6-Bis(1,1-dimethylethyl)-4-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]thio]phenol

Product 1

HCID 199006572,6-Bis(1,1-dimethylethyl)-4-[[5-(methylsulfinyl)-1,3,4-thiadiazol-2-yl]thio]-phenolYield 61.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,6-bis(1,1-dimethylethyl)-4-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]thio]phenol (0.25 g, 0.68 mmol) and sodium perborate (0.11 g, 0.71 mmol) in acetic acid (20 mL) is stirred at room temperature for 7 hours then stored at 0° C. overnight. The reaction mixture is diluted with ether and washed three times with water, then with a saturated solution of sodium bicarbonate and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a white solid which is chromatographed on silica gel eluting with a gradient of ethyl acetate:hexane (1:9, 2:8, 3:7, then 1:1) yielding 0.16 g (61%) of 2,6-bis(1,1-dimethylethyl)-4-[[5-(methylsulfinyl)-1,3,4-thiadiazol-2-yl]thio]-phenol; mp 162.0°-163.5° C.

Workup

  1. washwashed three times with water
  2. customDrying the organic phase
  3. customover magnesium sulfate and evaporation
  4. customgives a white solid which
  5. customis chromatographed on silica gel eluting with a gradient of ethyl acetate:hexane (1:9, 2:8, 3:7

Sources & evidence

ORD record
ord-3a67496a32a64d589d686448df6c8475
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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