Diethyl Ether → 2,6-Di(tert-butyl)-4-[5-(methylsulfanyl)-1,3,4-thiadiazol-2-yl]benzenol

HRID 466061Notes

Reaction equation

[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:16]2[S:20][C:19](=[S:21])[NH:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[H-].[Na+].IC.[CH3:26]COCC>O1CCCC1>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([C:16]2[S:20][C:19]([S:21][CH3:26])=[N:18][N:17]=2)[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

5-[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione (3.0 g, 0.0093 mole) in tetrahydrofuran (15 ml) is added dropwise to a stirred 0° C. suspension of sodium hydride (0.37 g of a 60% dispersion in mineral oil, 0.0093 mole) in tetrahydrofuran (15 ml) under nitrogen. After 30 minutes, a solution of iodomethane (1.5 g, 0.0102 mole) in tetrahydrofuran (5 ml) is added dropwise. After stirring one hour at 0° C., ether (20 ml) is added and the resulting mixture is washed with aqueous 2M HCl (10 ml), saturated aqueous NaCl, and dried over MgSO4. Filtration and concentration in vacuo, followed by recrystallization from ether/hexane gives 2.6 g of 2,6-bis(1,1-dimethylethyl)-4-[5-(methylthio)-1,3,4-thiadiazol-2-yl]phenol (3.1 g, theor., 83%), mp 122°-122.5° C.

Workup

washthe resulting mixture is washed with aqueous 2M HCl (10 ml), saturated aqueous NaCl
dry with materialdried over MgSO4
filtrationFiltration and concentration in vacuo
customfollowed by recrystallization from ether/hexane

Sources & evidence

ORD record: ord-d767d136a64342a49ba04411a0b006f5
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05155122

Reaction notes

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