Hydrochloric Acid → 3-Mercapto-4-cyclohexylphenylglyoxylic acid

HRID 26555

Reaction equation

HRID 26555 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 evapoated 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 6N 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. dissolutionThe residue is dissolved in 35 ml
  9. additionof boiling ethanol to which is added gradually 13 g
  10. temperatureThe reaction is refluxed an additional hour
  11. customevaporated to dryness in vacuo
  12. dissolutionThe residue is dissolved in water
  13. extractionextracted with ether
  14. extractionextracted with ether
  15. washThe ether is washed with water
  16. dry with materialdried over sodium sulfate
  17. customevaporated to dryness

Sources & evidence

ORD record
ord-3c5ec23170ba40e497c7ce202bc39879
Source dataset
uspto-grants-1979_04
Patent number
US04150148

Linked notes

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