Hydrogen Peroxide → 2,6-Bis(1,1-dimethylethyl)-4-[5-(methylsulfinyl)-1,3,4-thiadiazol-2-yl]phenol

HRID 1493012Notes

Reaction equation

[OH:1]O.[CH3:3][C:4]([C:7]1[CH:12]=[C:11]([C:13]2[S:14][C:15]([S:18][CH3:19])=[N:16][N:17]=2)[CH:10]=[C:9]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:8]=1[OH:24])([CH3:6])[CH3:5]>C(O)(=O)C>[CH3:21][C:20]([C:9]1[CH:10]=[C:11]([C:13]2[S:14][C:15]([S:18]([CH3:19])=[O:1])=[N:16][N:17]=2)[CH:12]=[C:7]([C:4]([CH3:3])([CH3:5])[CH3:6])[C:8]=1[OH:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

30% aqueous hydrogen peroxide (1.7 g, 0.015 mole) is added to a stirred solution of 2,6-bis(1,1-dimethylethyl)-4-[5-(methylthio)-1,3,4-thiadiazol-2-yl]-phenol (5.0 g, 0.015 mole) in glacial acetic acid (20 ml). The resulting mixture is heated to 90° C. for three hours. The mixture is cooled and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, 25% ethyl acetate/hexane eluent) to provide a solid which is recrystallized from ethyl acetate/hexane to give 1.4 g of 2,6-bis(1,1-dimethylethyl)-4-[5-(methylsulfinyl)-1,3,4-thiadiazol-2-yl]-phenol (5.3 g theor., 26%), mp 141.2° C.

Workup

temperatureThe mixture is cooled
concentrationconcentrated in vacuo
customThe residue is purified by flash chromatography (SiO2, 25% ethyl acetate/hexane eluent)
customto provide a solid which
customis recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-a4ad2b932ceb41bfb4a837403760a671
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05376670

Reaction notes

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