Hydrochloric Acid → 1-Dimethylamino-3-(4-fluorophenyl)-3-phenylthio-2-propene

HRID 845153Notes

Reaction equation

HRID 845153 reaction equation
[F: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.C(OCC)C>[CH3:12][N:11]([CH3:13])[CH2:10][CH:9]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[S:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 6005393-(Dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 541853621-Dimethylamino-3-(4-fluorophenyl)-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-fluorophenyl)-3-dimethylamino-2-propen-1-one (10 g), phosphorus oxychloride (4.76 cc), thiophenol (5.57 cc) and sodium cyanoborohydride (1.92 g), a residue is obtained which is taken up in chloroform. The solution is then 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 pressured (2.7 kPa) at 30° C. A residue is obtained which is dissolved in isopropanol (30 cc). A 3N solution (12 cc) of hydrochloric acid gas in ethyl ether is added to this solution. The solid which precipitates is separated off by filtration and recrystallised from isopropanol (30 cc). In this way 1-dimethylamino-3-(4-fluorophenyl)-3-phenylthio-2-propene (E) hydrochloride (3.3 g) is obtained in the form of a white solid melting at 160° 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 pressured (2.7 kPa) at 30° C
  8. customA residue is obtained which
  9. customThe solid which precipitates
  10. customis separated off by filtration
  11. customrecrystallised from isopropanol (30 cc)

Sources & evidence

ORD record
ord-997d1050156549a6bb44af04b6924ad8
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

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