4-Bromo-2,6-di-tert-butylphenol → 2,6-Bis(1,1-dimethylethyl)-4-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]thio]phenol

HRID 1029541노트

반응식

HRID 1029541 반응식
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([OH:12])=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:3]=1.[CH3:17][S:18][C:19]1[S:23][C:22]([SH:24])=[N:21][N:20]=1.N12CCCN=C1CCCC=C2>CN(C)C=O.CCOCC>[CH3:9][C:8]([C:6]1[CH:7]=[C:2]([S:24][C:22]2[S:23][C:19]([S:18][CH3:17])=[N:20][N:21]=2)[CH:3]=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=1[OH:12])([CH3:11])[CH3:10]

참가 물질

6

반응물 3

HCID 708294-Bromo-2,6-di-tert-butylphenolHCID 219795291,8-Diazabicyclo(5.4.0)undecen-7-eneHCID 1785036205-methylsulfanyl-1,3,4-thiadiazole-2-thiol

생성물 1

HCID 199006582,6-Bis(1,1-dimethylethyl)-4-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]thio]phenol수율 18.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-bromo-2,6-di-t-butylphenol (3.0 g, 10.5 mmol), 5-methylthio-1,3,4-thiadiazole-2-thiol (2.0 g, 12.2 mmol), and 1,8-diazabicyclo-[5.4.0]undecen-7-ene (1.8 mL, 12.0 mmol) in dimethylformamide (120 mL) is stirred at 55° to 70° C. for 48 hours. The reaction mixture is cooled and diluted with ether then washed four times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a solid residue which is crystallized from ethyl acetate/hexane yielding 2.4 g (63%) of analytically pure light brown platelets; mp 144.0°-145.0° C. The mother liquor is chromatographed on silica gel eluting with 1:9 then 2:8 ethyl acetate:hexane to yield an additional 0.7 g (18%) of 2,6-bis(1,1-dimethylethyl)-4-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]thio]phenol.

후처리

  1. temperatureThe reaction mixture is cooled
  2. washthen washed four times with water
  3. customDrying the organic phase
  4. customover magnesium sulfate and evaporation
  5. customgives a solid residue which
  6. customis crystallized from ethyl acetate/hexane yielding 2.4 g (63%) of analytically pure light brown platelets
  7. customThe mother liquor is chromatographed on silica gel eluting with 1:9

출처 및 근거

ORD 기록
ord-dc7916bb8f1a43a7a0df1a7ec229bc90
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102897

반응 노트

불러오는 중…