Hydrochloric Acid → HCID 15114333, compound

HRID 1199242Notes

Reaction equation

HRID 1199242 reaction equation
[CH2:1]([S:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([Cl:15])[C:7]=1Cl)(=[O:5])=[O:4])[CH3:2].[CH2:17]([SH:19])[CH3:18].[OH-].[Na+].Cl.[S:23](=O)(=O)(O)O>O.C(Cl)CCl.CO>[CH2:17]([S:19][C:7]1[C:8]([Cl:15])=[C:9]([CH:13]=[CH:14][C:6]=1[S:3][CH2:1][CH3:2])[C:10]([OH:12])=[O:11])[CH3:18].[Cl:15][C:8]1[C:7]([CH2:17][CH3:18])=[C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[S:23]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 6343EthanethiolHCID 14798Sodium HydroxideHCID 27642492,3-Dichloro-4-(ethanesulfonyl)benzoic acid

Product 2

HCID 15114333HCID 15114333, compoundHCID 178437384HCID 178437384, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the 4-ethylsulfonyl-2,3-dichlorobenzoic acid prepared in Example 3 (0.2 mole), ethyl mercaptan (0.8 mole), sodium hydroxide (1 mole) in water (300 ml) was heated at reflux for 24 hours. After cooling, the reaction mixture was acidified with concentrated hydrochloric acid and extracted with methylene chloride. The layers were separated, and the methylene chloride layer was dried over magnesium sulfate. Evaporation of the methylene chloride in vacuo then afforded a mixture of the acids which were esterified to the methyl esters with methanol and sulfuric acid in ethylene dichloride by the procedure of Clinton and Lawkowski, J. Amer. Chem. Soc., 70, 3135 (1948). The esters were then separated via standard chromatographic techniques. Basic hydrolysis of each methyl ester then afforded the 3,4-bis-ethylthio-2-chlorobenzoic acid, m.p. 73°-75° C. and 2-chloro-4-ethylsulfonyl-3-ethylthio-benzoic acid oil.

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. customThe layers were separated
  5. dry with materialthe methylene chloride layer was dried over magnesium sulfate
  6. customEvaporation of the methylene chloride in vacuo
  7. customthen afforded
  8. additiona mixture of the acids which
  9. customThe esters were then separated via standard chromatographic techniques
  10. customBasic hydrolysis of each methyl ester

Sources & evidence

ORD record
ord-1fe14d30331a4fe1ad33c58a73205cb5
Source dataset
uspto-grants-1990_02
Patent number
US04898973

Reaction notes

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