Itaconic acid → HCID 22051563, compound

HRID 597095Notes

Reaction equation

HRID 597095 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].[C:16]([OH:24])(=[O:23])[C:17]([CH2:19][C:20](O)=[O:21])=[CH2:18]>O>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([N:6]2[CH2:18][CH:17]([C:16]([OH:24])=[O:23])[CH2:19][C:20]2=[O:21])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-

Product 1

HCID 22051563HCID 22051563, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

229 g (1 mole) of 3,5-bis-(trifluoromethyl)-aniline and 136.5 g (1.05 moles) of itaconic acid are stirred in 55 ml of water during 24 hours at 200° C in an autoclave. The reaction mixture is subsequently cooled to 20° C and 2 liters of cold water are added. Two liters of water are then evaporated, and the reaction mixture is again cooled to 20° C. The crystals that have precipitated are filtered off, dried, dissolved in 400 ml of diethyl ether and precipitated with 600 ml of n-hexane. There is obtained 242 g (71% of theory) of 1-(3,5-bis-trifluoromethylphenyl)-2-oxo-pyrrolidine-4-carboxylic acid; m.p. 108°-9° C.

Workup

  1. customTwo liters of water are then evaporated
  2. temperaturethe reaction mixture is again cooled to 20° C
  3. customThe crystals that have precipitated
  4. filtrationare filtered off
  5. customdried
  6. dissolutiondissolved in 400 ml of diethyl ether
  7. customprecipitated with 600 ml of n-hexane

Sources & evidence

ORD record
ord-dcb1d6556f1f42ce995e60af9fb8ed54
Source dataset
uspto-grants-1977_03
Patent number
US04013445

Reaction notes

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