Thiophenol → 1-Dimethylamino-3-phenyl-3-phenylthio-2-propene

HRID 845150Notes

Reaction equation

HRID 845150 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.[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([BH3-])#N.[Na+]>P(Cl)(Cl)(Cl)=O>[CH3:1][N:2]([CH3:13])[CH2:3][CH:4]=[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[S:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 541931701-Dimethylamino-3-phenyl-3-phenylthio-2-propene

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (80 g), phosphorus oxychloride (40 cc), thiophenol (50.3 cc) and sodium cyanoborohydride (16 g), and crystallising the (Z)-isomer, a yellow solid is isolated after evaporation of the mother liquors under reduced pressure (2.7 kPa) at 30° C. followed by crystallisation of the residue obtained from a mixture of acetone and ethyl ether (25/75 by volume); the solid is recrystallised from methyl ethyl ketone (230 cc). 1-Dimethylamino-3-phenyl-3-phenylthio-2-propene (E) hydrochloride (14.3 g) is thus obtained in the form of a white solid melting at 146°-147° C.

Workup

  1. customcrystallising the (Z)-isomer
  2. customa yellow solid is isolated
  3. customafter evaporation of the mother liquors under reduced pressure (2.7 kPa) at 30° C.
  4. customfollowed by crystallisation of the residue
  5. customobtained from a mixture of acetone and ethyl ether (25/75 by volume)
  6. customthe solid is recrystallised from methyl ethyl ketone (230 cc)

Sources & evidence

ORD record
ord-5f17f24339934a9d89f744c2037afce9
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

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