Thioglycolic Acid → 2-(2,5-Dichlorophenyl)-2-mercaptoacetic acid

HRID 248599

Reaktionsgleichung

Reaktionsgleichung von HRID 248599
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[Cl:9].[OH-].[K+].[C:12]([OH:16])(=[O:15])[CH2:13][SH:14].ClCC([O-])=O.[Na+]>CN1CCCC1=O>[Cl:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[CH:13]([SH:14])[C:12]([OH:16])=[O:15]

Komponenten

6

Edukt 4

HCID 1133Thioglycolic AcidHCID 14797Potassium HydroxideHCID 150332-Bromo-1,4-dichlorobenzeneHCID 23665759Sodium chloroacetate

Produkt 1

HCID 224923292-(2,5-Dichlorophenyl)-2-mercaptoacetic acidAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Using the same procedure as in Example 8, 45.2 g (0.2 mol) of 1-bromo-2,5-dichlorobenzene, 23.7 g (0.4 mol) of 95% potassium hydroxide, 18.4 g (0.2 mol) of thioglycolic acid and 320 g of N-methyl-2-pyrrolidone were added, followed by stirring at 140° to 150° C. for 2 hours. Then, 30.4 g (0.26 mol) of sodium monochloroacetate was added to the reaction solution, followed by stirring at 90° C. for 1 hour. After distilling off the solvent, 300 g of water and 50 g of toluene were added for layer separation. To the water layer was added 45 g of concentrated hydrochloric acid, and the mixture was cooled to room temperature. The resulting crystal was filtered and dried to yield 34.0 g of 2,5-dichlorophenylthioglycolic acid with a yield of 71.7%. The results are given in Table 2.

Aufarbeitung

  1. additionwere added
  2. stirringby stirring at 90° C. for 1 hour
  3. distillationAfter distilling off the solvent, 300 g of water and 50 g of toluene
  4. additionwere added for layer separation
  5. additionTo the water layer was added 45 g of concentrated hydrochloric acid
  6. filtrationThe resulting crystal was filtered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9915deca733e4f2b99d128d10388e304
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05210291

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