Hydrochloric Acid → HCID 13336751, compound

HRID 1462907Notes

Reaction equation

HRID 1462907 reaction equation
S[CH2:2][CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH:7]1[C:16]([OH:18])=[O:17])=[O:5].[OH-:19].[Na+].II.[S:23]([O-])([O-])(=O)=[S:24].[Na+].[Na+].Cl>O.C(O)C>[O:5]=[C:4]([N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH:7]1[C:16]([OH:18])=[O:17])[CH2:3][CH2:2][S:23][S:24][CH2:2][CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH:7]1[C:16]([OH:18])=[O:17])=[O:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807Iodine2×HCID 14798Sodium Hydroxide2×HCID 24477Sodium ThiosulfateHCID 13336749HCID 13336749, compound

Product 1

HCID 13336751HCID 13336751, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(±)-1,2,3,4-Tetrahydro-1-(3-mercapto-1-oxopropyl)-2-quinolinecarboxylic acid (13.27 g) was suspended in water (125 ml) and the pH was adjusted to 6-7 by the addition of 2 N sodium hydroxide. To the resulting clear solution was added 0.5 M iodine in 95% ethanol dropwise while maintaining the pH at 6.5 by the slow addition of 2 N sodium hydroxide. When a yellow color remained for at least five minutes, addition of the iodine solution was termined and the color was discharged with saturated aqueous sodium thiosulfate. The mixture was then acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The combined organic layer was washed with 10% hydrochloric acid and water, dried over magnesium sulfate, and concentrated under reduced pressure to yield 11 g of (±) 1,1'-[dithiobis(1-oxo-3,1-propanediyl]-bis-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid, m.p. 92°-103° (dec).

Workup

  1. temperaturewhile maintaining the pH at 6.5
  2. waitWhen a yellow color remained for at least five minutes
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with 10% hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53de944d66b940739d2b9beec9275c18
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

Loading…