Acetic Acid → 2-(2-Mercapto-2-methylpropylamino)-1-[2-(4-pentenylthio)-2-methylpropylamino]-benzene

HRID 1090038ノート

反応式

HRID 1090038 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]([SH:13])([CH3:12])[CH3:11].[CH2:14]([S:19][C:20]([CH3:24])([CH3:23])[CH:21]=O)[CH2:15][CH2:16][CH:17]=[CH2:18].C(O)(=O)C.C([BH3-])#N.[Na+].Cl>CO>[SH:13][C:10]([CH3:11])([CH3:12])[CH2:9][NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:21][C:20]([S:19][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])([CH3:24])[CH3:23]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 100129272-Amino-1-(2-mercapto-2-methylpropylamino)benzeneHCID 102412662-(4-Pentenylthio)-2-methylpropanal

生成物 1

HCID 100436132-(2-Mercapto-2-methylpropylamino)-1-[2-(4-pentenylthio)-2-methylpropylamino]-benzene収率 97%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2-Amino-1-(2-mercapto-2-methylpropylamino)benzene (0.155 g, 7/9×10-4 mol) and 0.30 g (1.74×10-3 mol, 220 M%) of 2-(4-pentenylthio)-2-methylpropanal were dissolved in 40 ml methanol. Acetic acid (0.09 ml, 1.59×10-3 mol, 200 M%) was added followed by 0.155 g (2.3×10-3 mol, 300 M%) sodium cyanoborohydride. The reaction was stirred at room temperature under nitrogen for 17 hr, then 20 ml 0.5 M HCl was added and the mixture was extracted with 2×40 ml diethyl ether. The ether layer was washed with 30 ml saturated NaCl solution and dried (Na2SO4), and the solvent was removed on the rotary evaporator. The product was purified by radial chromatography on a 2 mm silica plate eluting with 50 ml 100% hexane and 100 ml 90% hexane/ether to give 0.27 g (97% yield) of 2-(2-mercapto-2-methylpropylamino)-1-[2-(4-pentenylthio)-2-methylpropylamino]-benzene as an oil.

後処理

  1. extractionthe mixture was extracted with 2×40 ml diethyl ether
  2. washThe ether layer was washed with 30 ml saturated NaCl solution
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed on the rotary evaporator
  5. customThe product was purified by radial chromatography on a 2 mm silica plate
  6. washeluting with 50 ml 100% hexane and 100 ml 90% hexane/ether

出典と根拠

ORDレコード
ord-fc1d405ba6f94c198017f8bedd5e3ef4
出典データセット
uspto-grants-1992_01
特許番号
US05080884

反応ノート

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