Hydrochloric Acid → 3-Mercapto-4-cyclohexylphenylglyoxylic acid

HRID 236828Notes

Reaction equation

HRID 236828 reaction equation
N[C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([O:17]CC)=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl.N([O-])=O.[Na+].O(CC)C([S-])=[S:28].[K+]>O>[SH:28][C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2735045Potassium ethylxanthateHCID 20515218Ethyl 3-amino-4-cyclohexylphenylglyoxylateHCID 23668193Sodium Nitrite

Product 1

HCID 205151653-Mercapto-4-cyclohexylphenylglyoxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 17.3 g. of ethyl 3-amino-4-cyclohexylphenylglyoxylate in 11.1 ml. of concentrated hydrochloric acid and 20 g. of ice is added 4.1 g. of sodium nitrite in 2 ml. of water. This mixture is stirred for 10 min. and then added gradually to an ice cold solution of 10.3 g. of potassium ethyl xanthate in 14 ml. of water. The reaction is gradually heated over 45 minutes to 50° C. and stirred an additional 45 minutes. The mixture is then cooled, extracted with ether which is then washed with water, dilute sodium hydroxide and water, dried over sodium sulfate and evaporated in vacuo. The residue is dissolved in 35 ml. of boiling ethanol to which is added gradually 13 g. of potassium hydroxide. The reaction is refluxed an additional hour and then evaporated to dryness in vacuo. The residue is dissolved in water and extracted with ether. The alkaline phase is acidified with 6 N sulfuric acid and extracted with ether. The ether is washed with water, dried over sodium sulfate and evaporated to dryness to obtain 3-mercapto-4-cyclohexylphenylglyoxylic acid.

Workup

  1. additionof ice is added 4.1 g
  2. temperatureThe reaction is gradually heated over 45 minutes to 50° C.
  3. stirringstirred an additional 45 minutes
  4. temperatureThe mixture is then cooled
  5. extractionextracted with ether which
  6. washis then washed with water, dilute sodium hydroxide and water
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. dissolutionThe residue is dissolved in 35 ml
  10. additionof boiling ethanol to which is added gradually 13 g
  11. temperatureThe reaction is refluxed an additional hour
  12. customevaporated to dryness in vacuo
  13. dissolutionThe residue is dissolved in water
  14. extractionextracted with ether
  15. extractionextracted with ether
  16. washThe ether is washed with water
  17. dry with materialdried over sodium sulfate
  18. customevaporated to dryness

Sources & evidence

ORD record
ord-ed4e8ad4cadb4f17ab6d79a3ee47b723
Source dataset
uspto-grants-1979_06
Patent number
US04157449

Reaction notes

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