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

HRID 1493010Notes

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-4010a61586c44df885154007b65dae71
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05376670

Reaction notes

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