Hydrochloric Acid → HCID 23312049, compound

HRID 745793Notes

Reaction equation

HRID 745793 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([NH:10][C:11]1[CH:12]=[C:13]([S:19]([C:22]2[CH:23]=[C:24]([OH:30])[C:25]([OH:29])=[CH:26][C:27]=2[CH3:28])(=[O:21])=[O:20])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])(=[O:9])[CH3:8].C([O:33][C:34](=[O:38])[CH:35](Cl)Cl)C.Cl>COCCOC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CC(C)=O>[C:7]([NH:10][C:11]1[CH:12]=[C:13]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]3[O:29][CH:35]([C:34]([OH:38])=[O:33])[O:30][C:24]=3[CH:23]=2)(=[O:21])=[O:20])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])(=[O:9])[CH3:8]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10808Ethyl dichloroacetate2×HCID 11430Potassium Carbonate2×HCID 23312056HCID 23312056, compound

Product 1

HCID 23312049HCID 23312049, compound

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of 72.8 g (526 mmol) of freshly calcined potassium carbonate in 300 ml of 1,2-dimethoxyethane is stirred under nitrogen for 10 minutes using a high-speed stirrer and then, while stirring normally, 37.0 g (105.3 mmol) of 4-(3-acetamido-4-methoxyphenylsulphonyl)-5-methyl-1,2-benzenediol, 16.5 g (105.3 mmol) of dichloroacetic acid ethyl ester and 3 g of tetrabutylammonium bromide are added. The mixture is boiled under reflux, 300 ml of acetone are added, the whole is boiled under reflux for 3 more hours, a further 60 g of potassium carbonate and 16.5 g of dichloroacetic acid ethyl ester are added, and the whole is boiled under reflux for 9 more hours. The reaction mixture is poured into water and acidified to pH 1-2 with hydrochloric acid. Some of the solvent is evaporated off in vacuo and the aqueous phase remaining is extracted with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride solution, dried over sodium sulphate and concentrated by evaporation in a rotary evaporator. The residue is recrystallised four times from acetonitrile, yielding 5-(3-acetamido-4-methoxyphenylsulphonyl)-6-methyl-1,3-benzodioxole-2-carboxylic acid in the form of white crystals having a melting point of 230° (sintering at 150°).

Workup

  1. stirringwhile stirring normally
  2. temperatureunder reflux
  3. temperatureunder reflux for 3 more hours
  4. temperatureunder reflux for 9 more hours
  5. customSome of the solvent is evaporated off in vacuo
  6. extractionthe aqueous phase remaining is extracted with ethyl acetate
  7. washThe combined organic phases are washed with water and saturated sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated by evaporation in a rotary evaporator
  10. customThe residue is recrystallised four times from acetonitrile

Sources & evidence

ORD record
ord-f3272ae30d7c4194bbfd3db73261b7b2
Source dataset
uspto-grants-1986_07
Patent number
US04600709

Reaction notes

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