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 1029541ノート

反応式

HRID 1029541 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dc7916bb8f1a43a7a0df1a7ec229bc90
出典データセット
uspto-grants-1992_04
特許番号
US05102897

反応ノート

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