Water → HCID 69000022, compound

HRID 1811544Notes

Reaction equation

HRID 1811544 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH3:20])[C:14]=2[Cl:21])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1.[OH-].[K+:23].O>CC(C)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH3:20])[C:14]=2[Cl:21])=[C:6]([CH2:8][C:9]([O-:11])=[O:10])[CH:7]=1.[K+:23]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 23642285HCID 23642285, compound

Product 1

HCID 69000022HCID 69000022, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of 5-Methyl-2-(2′,4′-dichloro-3′-methylanilino)phenylacetic acid (15.42 mmoles) in acetone is heated to reflux temperature and allow to stir for 10 min at ca. 55° C. The resulting solution is slightly cooled to 50° C. and filtered hot over Whatman glasfiber filter. The filter is washed with acetone at 50° C. The filtrate is heated to 50° C. and a mixture of potassium hydroxide 45% (14.65 mmoles) (0.95 eq.) and water is dropwise added over ca. 15 min. The dropping funnel is rinsed with water and acetone. The resulting suspension is stirred at 50° C. for 30 min. The slurry is then allowed to cool to 25° C. over ca. 2 hours. The suspension is stirred over night at room temperature and filtered. The filter cake is washed in three portions. The crystals are dried first for 3 h at 50° C./10 mbar and then further for 17 h at 80° C./10 mbar to yield a white powder, m.p. 315-317° C., 326.9° C., melting enthalpy 29 J/g.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature
  3. temperatureThe resulting solution is slightly cooled to 50° C.
  4. filtrationfiltered hot over Whatman glasfiber
  5. filtrationfilter
  6. washThe filter is washed with acetone at 50° C
  7. temperatureThe filtrate is heated to 50° C.
  8. additionis dropwise added over ca. 15 min
  9. washThe dropping funnel is rinsed with water and acetone
  10. stirringThe resulting suspension is stirred at 50° C. for 30 min
  11. temperatureto cool to 25° C. over ca. 2 hours
  12. stirringThe suspension is stirred over night at room temperature
  13. filtrationfiltered
  14. washThe filter cake is washed in three portions
  15. customThe crystals are dried first for 3 h at 50° C./10 mbar
  16. customfurther for 17 h at 80° C./10 mbar to yield a white powder, m.p. 315-317° C., 326.9° C.

Sources & evidence

ORD record
ord-3fb6c6972a86481da333bd0415e25e0c
Source dataset
uspto-grants-2013_01
Patent number
US08362294B2

Reaction notes

Loading…