Hydrochloric Acid → 3-(4-Bromophenyl)-1-dimethylamino-3-phenylthio-2-propene

HRID 845154Notes

Reaction equation

HRID 845154 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([BH3-])#N.[Na+].[OH-].[Na+].Cl>C(Cl)(Cl)Cl.C(O)(C)C.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([S:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:9][CH2:10][N:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 6172441-(4-Bromophenyl)-3-(dimethylamino)-2-propen-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 537682463-(4-Bromophenyl)-1-dimethylamino-3-phenylthio-2-propene

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

By using a method similar to that described in Example 35, but starting from 1-(4-bromophenyl)-3-dimethylamino-2-propen-1-one (10 g), phosphorus oxychloride (3.64 g), thiophenol (4.2 cc) and sodium cyanoborohydride (1.47 g), a residue is obtained which is taken up in chloroform. The solution is adjusted to pH 10 by adding a concentrated aqueous solution of sodium hydroxide. The organic phase is separated and then 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 (2.6 kPa) at 30° C. to give a residue which is dissolved in isopropanol (30 cc). A 3N ether solution (13 cc) of hydrochloric acid gas is added to the solution obtained. The white solid which precipitates is separated off by filtration and recrystallised twice from isopropanol (40 cc). In this way 3-(4-bromophenyl)-1-dimethylamino-3-phenylthio-2-propene (E) hydrochloride (4.8 g) is obtained in the form of white crystals melting at 187° C.

Workup

  1. customa residue is obtained which
  2. customThe organic phase is separated
  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 (2.6 kPa) at 30° C.
  8. customto give a residue which
  9. customobtained
  10. customThe white solid which precipitates
  11. customis separated off by filtration
  12. customrecrystallised twice from isopropanol (40 cc)

Sources & evidence

ORD record
ord-e678f67edf574e429160f4ee5eccd170
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

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