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

HRID 1789099Notes

Reaction equation

HRID 1789099 reaction equation
[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.Cl[C:20]1[CH:25]=[CH:24][C:23](S)=[CH:22][CH:21]=1.C([BH3-])#N.[Na+].Cl.[CH2:32]([OH:34])C>C(OCC)C>[CH:20]1([CH:32]([OH:34])[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

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7815p-ChlorothiophenolHCID 24813Phosphorus oxychlorideHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.5 cc), p-chlorothiophenol (4.13 g) and sodium cyanoborohydride (1 g), and after evaporating the reaction mixture under reduced pressure (2.7 kPa) at 40° C., a residue is obtained, which is dissolved in ethanol (50 cc). A 3N solution (12 cc) of hydrochloric acid gas in ethyl ether is added to this solution. The precipitate formed is separated off by filtration and then recrystallised from ethanol (70 cc). In this way 3-(4-chlorophenylthio)-1-dimethylamino-3-phenylthio-2-propene (Z) hydrochloride (3.4 g) is obtained in the form of a white powder melting at 226° C.

Workup

  1. customafter evaporating the reaction mixture under reduced pressure (2.7 kPa) at 40° C.
  2. customa residue is obtained
  3. customThe precipitate formed
  4. customis separated off by filtration
  5. customrecrystallised from ethanol (70 cc)

Sources & evidence

ORD record
ord-76c9e3d8f8064427b92e1694b802ac91
Source dataset
uspto-grants-1987_08
Patent number
US04686309

Reaction notes

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