Hydrochloric Acid → Hydrochloric Acid

HRID 2414245Notes

Reaction equation

HRID 2414245 reaction equation
[CH:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=[C:3](N)[CH:2]=1.N([O-])=O.[Na+].O(CC)[C:16]([S-])=[S:17].[K+].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[K+].S(OC)(OC)(=O)=O.[ClH:37]>>[ClH:37].[CH3:16][S:17][C:2]1[CH:1]=[C:6]([CH:5]=[CH:4][CH:3]=1)[C:7]([OH:9])=[O:8]

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 2735045Potassium ethylxanthateHCID 23668193Sodium Nitrite

Product 2

HCID 313Hydrochloric AcidHCID 2203293-(Methylthio)benzoic Acid

Procedure

The aminobenzoic acid (54.8 g, 0.4 mol) was diazotized in the usual manner with sodium nitrite (27.6 g, 0.4 mol) and hydrochloric acid (40 mL) and the resulting diazonium salt solution poured into a hot (70° C.), freshly prepared solution of potassium ethyl xanthate (64.2 g, 0.4 mol) containing sodium carbonate (55.2 g, 0.4 mol) to neutralize acid in the diazonium salt solution. After the reaction was over, as indicated by the cessation of the evolution of gases, the mixture was cooled. It was then treated with potassium hydroxide (24.7 g, 0.44 mol) and dimethyl sulfate (50.4 g, 0.4 mol). The mixture was refluxed for 5 hours. On acidification with hydrochloric acid, the desired product was obtained (38.2 g, 57%). MS: 167.8 (M+1+).

Workup

  1. temperaturethe mixture was cooled
  2. temperatureThe mixture was refluxed for 5 hours

Sources & evidence

ORD record
ord-72776ee05ed24787a18917af6c8d7374
Source dataset
uspto-grants-2004_11
Patent number
US06812228B2

Reaction notes

Loading…