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

HRID 1493010노트

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HRID 1493010 반응식
[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]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 30370185-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazole-2(3H)-thione

생성물 1

HCID 46798982,6-Di(tert-butyl)-4-[5-(methylsulfanyl)-1,3,4-thiadiazol-2-yl]benzenol수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4010a61586c44df885154007b65dae71
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05376670

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