Hydrochloric Acid → 1-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

HRID 845155

反応式

HRID 845155 の反応式
[CH3:1][N:2]([CH3:13])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.P(Cl)(Cl)(Cl)=O.Br[C:20]1[CH:25]=[CH:24][C:23](S)=[CH:22][CH:21]=1.[C:27]([BH3-])#N.[Na+].[OH-:31].[Na+].Cl>C(Cl)(Cl)Cl.C(O)C.CCOCC>[CH:20]1([CH:27]([OH:31])[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH2:3][N:2]([CH3:13])[CH3:1])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 660494-BromothiophenolHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 538458471-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒HCID 6212Chloroform溶媒

実験手順

By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.47 cc), 4-bromothiophenol (5.39 g) and sodium cyanoborohydride (1 g), a chestnut-coloured residue is obtained which is taken up in chloroform. The solution is made alkaline to pH 10 with an aqueous solution of sodium hydroxide. After separation of the chloroform phase, the aqueous phase is extracted with methylene chloride. The organic phases are collected, dried over sodium sulphate, filtered and then evaporated to dryness under reduced pressure (2.7 kPa) at 30° C. A residue is obtained which is dissolved in ethanol (60 cc). A 3N ether solution (7.7 cc) of hydrochloric acid gas is added to this solution. The white solid which precipitates is separated off by filtration and recrystallised from a mixture of isopropanol and methanol (60/40 by volume). In this way 3-(4-bromophenylthio)-1-dimethylamino-3-phenyl-2-propene (Z) hydrochloride (1.8 g) is obtained in the form of a white solid melting at 252° C.

後処理

  1. customa chestnut-coloured residue is obtained which
  2. customAfter separation of the chloroform phase
  3. extractionthe aqueous phase is extracted with methylene chloride
  4. customThe organic phases are collected
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure (2.7 kPa) at 30° C
  8. customA residue is obtained which
  9. customThe white solid which precipitates
  10. customis separated off by filtration
  11. customrecrystallised from a mixture of isopropanol and methanol (60/40 by volume)

出典と根拠

ORDレコード
ord-054f3a3e9725410bb4a0273992a16bb6
出典データセット
uspto-grants-1988_07
特許番号
US04755599

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