2-Chloro-5-nitrobenzoic acid → 2-((Carboxymethyl)thio)-5-nitrobenzoic acid

HRID 1283948Notes

Reaction equation

HRID 1283948 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14](=[O:17])(O)[O-:15].[Na+].[C:19](O)(=[S:22])CO.[Na]>CCOCCO>[C:14]([CH2:19][S:22][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([OH:15])=[O:17]

Participants

6

Reactant 4

HCID 172872-Chloro-5-nitrobenzoic acidHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 178521514HCID 178521514, compound

Product 1

HCID 30153152-((Carboxymethyl)thio)-5-nitrobenzoic acidYield 86.3%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

In a 5 liter flask equipped with an impervious agitator, a reflux refrigerant and a thermometer, there are introduced 146 g (0.72 mole) of 2-chloro-5-nitro-benzoic acid and 2200 ml of cellosolve. There is obtained a solution to which is added 181 g of sodium bicarbonate and 66 g of thio-glycolic acid. The mixture is refluxed. There is very rapid precipitation of the sodium salt of the carboxymethylthio acid formed. After 3 1/2 hours of reflux, the heating is stopped, and the sodium salt is cooled, drained and washed on a filter with 200 ml of cellosolve. This salt is then redissolved in water and the acid is precipitated with 145 ml of concentrated hydrochloric acid. It is drained, washed with water until the chloride ions are eliminated and dried at 50° C. There are obtained 159 g (yield: 86%) of 2-carboxymethylthio-5-nitro-benzoic acid (m.p.: 216°-217° C).

Workup

  1. customIn a 5 liter flask equipped with an impervious agitator
  2. customThere is obtained a solution to which
  3. temperatureThe mixture is refluxed
  4. customprecipitation of the sodium salt of the carboxymethylthio acid
  5. customformed
  6. temperatureAfter 3 1/2 hours of reflux
  7. washwashed on
  8. filtrationa filter with 200 ml of cellosolve
  9. dissolutionThis salt is then redissolved in water
  10. customthe acid is precipitated with 145 ml of concentrated hydrochloric acid
  11. washwashed with water until the chloride ions
  12. customdried at 50° C

Sources & evidence

ORD record
ord-392619f30ede4462a1106a80b7a8827a
Source dataset
uspto-grants-1976_08
Patent number
US03976780

Reaction notes

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