Hydrochloric Acid → 2-Mercapto-6-acetylbenzoic acid

HRID 1464197

Reaction equation

HRID 1464197 reaction equation
N[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[O:13])[CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].Cl.N([O-])=O.[Na+].[S-:19][S-].[Na+].[Na+]>O>[SH:19][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[O:13])[CH3:12])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 89870Sodium disulfideHCID 190894012-Acetyl-6-aminobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 190893912-Mercapto-6-acetylbenzoic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

10.2 g of 2-amino-6-acetylbenzoic acid was converted into a diazonium salt with a mixture of 14.2 ml of concentrated hydrochloric acid, 40 ml of water and 4.3 g of sodium nitrite, and the diazonium salt was gradually added dropwise at a temperature of 0 to 5° C. to a sodium disulfide aqueous solution (prepared from 14.3 g of sodium sulfide.9H2O, 1.9 g of sulfur, 4.6 g of sodium hydroxide and 30 ml of water). After adding dropwise, the reaction liquor was stirred for 2 hours at room temperature to complete the reaction. The reaction liquor was poured into a large amount of water, and after adding concentrated hydrochloric acid thereto, the product was extracted with ethyl acetate. To the ethyl acetate layer, was added sodium hydrogencarbonate aqueous solution, and the content soluble in sodium hydrogencarbonate was extracted. To the resultant aqueous solution, was added 14.8 g of sodium pyrosulfate, and the mixture was refluxed for 30 minutes to complete the reaction. To the reaction liquor, was added concentrated hydrochloric acid, and the product was extracted with ethyl acetate. The extracted liquor was dried, and the solvent was distilled off under reduced pressure to obtain 10.1 g of 2-mercapto-6-acetylbenzoic acid at a yield of 90%.

Workup

  1. additionAfter adding dropwise
  2. customthe reaction
  3. extractionthe product was extracted with ethyl acetate
  4. additionTo the ethyl acetate layer, was added sodium hydrogencarbonate aqueous solution
  5. extractionthe content soluble in sodium hydrogencarbonate was extracted
  6. additionTo the resultant aqueous solution, was added 14.8 g of sodium pyrosulfate
  7. temperaturethe mixture was refluxed for 30 minutes
  8. customthe reaction
  9. extractionthe product was extracted with ethyl acetate
  10. customThe extracted liquor was dried
  11. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2e3646a1afce4634b6e380ab47603bf4
Source dataset
uspto-grants-1994_04
Patent number
US05302739

Linked notes

Loading…