Hydrochloric Acid → HCID 86734351, compound

HRID 1414269Notes

Reaction equation

HRID 1414269 reaction equation
[ClH:1].[CH2:2]([N:4]([CH2:35][CH3:36])[CH2:5][CH2:6][N:7]([S:28]([CH2:31][CH2:32][CH2:33][CH3:34])(=[O:30])=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[CH3:3].ClCl.Cl.[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH2:35]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][N:7]([S:28]([CH2:31][CH2:32][CH2:33][CH3:34])(=[O:30])=[O:29])[C:8]1[CH:9]=[CH:10][C:11]([C:14]([Cl:1])=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:13]=1)[CH3:36]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24526ChlorineHCID 86734352HCID 86734352, compound

Product 1

HCID 86734351HCID 86734351, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 6212ChloroformSolvent

Procedure

N-(2-Diethylaminoethyl)-4'-(β-phenylstyryl)butanesulfonanilide hydrochloride (10.5 g., 0.02 mole, refer to Procedure 51) is dissolved in a mixture of 300 ml. of carbon tetrachloride and 20 ml. of chloroform. The mixture is stirred and 39 ml. of a carbon tetrachloride solution containing 1.4 g. (0.02 mole) of chlorine is added thereto during 30 min. The mixture is kept at room temperature for an additional 30 min. and then refluxed for 1 hr. Vigorous evolution of hydrogen chloride gas is apparent during this period. The reaction mixture is allowed to cool and then neutralized with 100 ml. of aqueous 5% sodium hydroxide. The organic layer is separated, dried over magensium sulfate, and the solvent evaporated yielding 11.0 g. of the desired product. The material is purified by chromatography on an alumina column having dimensions 1 inch by 15 inches and eluting sequentially with 1:1 benzene-octane; benzene; benzene-chloroform, and finally with chloroform and collecting the eluate in 20 fractions. Fractions 15-19 are combined and the desired product recovered as the citrate salt, m.p. 65°-70°C.

Workup

  1. waitThe mixture is kept at room temperature for an additional 30 min.
  2. temperaturerefluxed for 1 hr
  3. temperatureto cool
  4. customThe organic layer is separated
  5. dry with materialdried over magensium sulfate
  6. customthe solvent evaporated
  7. customyielding 11.0 g

Sources & evidence

ORD record
ord-1f0c3439130942db8a7aac8d01da6ca7
Source dataset
uspto-grants-1977_01
Patent number
US04001229

Reaction notes

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