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Hydrochloric Acid → 4'-[13-(4-Chlorophenyl)tridec-12-ynylamino]-2-(phenylsulfonyl)acetophenone

HRID 2057676
Notes
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Reaction equation

HRID 2057676 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]2[CH:43]=[CH:42][C:37]([C:38](OC)=[O:39])=[CH:36][CH:35]=2)=[CH:16][CH:15]=1.Cl>O1CCCC1.COCCOC>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]2[CH:35]=[CH:36][C:37]([C:38](=[O:39])[CH2:3][S:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)(=[O:6])=[O:5])=[CH:42][CH:43]=2)=[CH:18][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 18369Methyl phenyl sulfoneHCID 24758Sodium hydrideHCID 20330962Methyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

Product 1

HCID 203309594'-[13-(4-Chlorophenyl)tridec-12-ynylamino]-2-(phenylsulfonyl)acetophenone

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 864 mg. of sodium hydride and 5.3 g. of methylphenylsulfone in 20 ml. of 1,2-dimethoxyethane is stirred at 60° C. for one hour under an atmosphere of argon. To this solution is added a solution of 5.0 g. of methyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate in 50 ml. of tetrahydrofuran and the reaction mixture is stirred at 60° C. for 1.5 hours. The mixture is cooled, poured onto ice, acidified with dilute hydrochloric acid to pH 3 and then extracted with chloroform. The organic layer is separated, washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated to dryness. The crude solid is chromatographed on silica gel, eluting with methylene chloride to yield 4'-[13-(4-chlorophenyl)tridec-12-ynylamino]-2-(phenylsulfonyl)acetophenone.

Workup

  1. additionTo this solution is added a solution of 5.0 g
  2. temperatureThe mixture is cooled
  3. additionpoured onto ice
  4. extractionextracted with chloroform
  5. customThe organic layer is separated
  6. washwashed with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe crude solid is chromatographed on silica gel
  10. washeluting with methylene chloride

Sources & evidence

ORD record
ord-90b493dc48064a9e8a82635af9383a9f
Source dataset
uspto-grants-1980_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04211783

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes