Hydrochloric Acid → HCID 53821217, compound

HRID 849272Notes

Reaction equation

HRID 849272 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH3:11][C:12]1=[C:13]([CH3:19])[C:14]([O:16][C:17]1=O)=[O:15].[ClH:20]>[OH-].[Na+].CC(N(C)C)=O>[CH3:11][C:12]1[C:17](=[O:16])[N:1]([C:2]2[CH:3]=[CH:4][C:5]([C:6]([Cl:20])=[O:8])=[CH:9][CH:10]=2)[C:14](=[O:15])[C:13]=1[CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 9784-Aminobenzoic AcidHCID 13010Dimethylmaleic anhydride

Product 1

HCID 53821217HCID 53821217, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

48 g (0.35 mol) of 4-aminobenzoic acid are dissolved in sodium hydroxide solution (14 g of NaOH in 300 ml of water). To that mixture there is added dropwise, with stirring, a solution of 44.2 g of dimethylmaleic acid anhydride in 300 ml of dimethylacetamide. The solution is then heated at 90° C. and, after 1.30 hours, 175 ml of aqueous hydrochloric acid (2N) are added. After the addition of hydrochloric acid, the solution is cooled to room temperature and the stirrer is switched off. The crystalline product that has precipitated is filtered off, washed with water and dried in vacuo at 60° C. Yield: 73.6 g (85.7%). Melting point: 230-231° C. 73.6 g of that intermediate are suspended in 700 ml of dry toluene. At 70° C., 32 ml of thionyl chloride are added dropwise. As soon as the evolution of gas has ceased (approx. 2 hours), the temperature is increased to 80° C. for 2 hours. After cooling, the solution is concentrated using a rotary evaporator. The solid residue is recrystallised from toluene and then dried at 60° C. Yield: 88%. Melting point: 199-200° C. 1H-NMR (CDCl3): 2.08 (s, CH3), 7.68 (d, phenyl), 8.20 (d, phenyl).

Workup

  1. additionTo that mixture there is added dropwise
  2. temperaturethe solution is cooled to room temperature
  3. customThe crystalline product that has precipitated
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried in vacuo at 60° C
  7. additionAt 70° C., 32 ml of thionyl chloride are added dropwise
  8. custom(approx. 2 hours)
  9. temperaturethe temperature is increased to 80° C. for 2 hours
  10. temperatureAfter cooling
  11. concentrationthe solution is concentrated
  12. customa rotary evaporator
  13. customThe solid residue is recrystallised from toluene
  14. customdried at 60° C

Sources & evidence

ORD record
ord-07b8453d980041d9a8aaed9d236320b5
Source dataset
uspto-grants-2000_01
Patent number
US06011149

Reaction notes

Loading…