Aniline → HCID 12952954, compound

HRID 1390134Notes

Reaction equation

HRID 1390134 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:8][N:7]([CH3:9])[C:6](=O)[N:5]1[CH3:11].P(Cl)(Cl)(Cl)=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28].C([O-])(=O)/C=C/C([O-])=O>C(Cl)(Cl)Cl.C(O)(C)C>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28].[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:8][N:7]([CH3:9])[C:6](=[N:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]1[CH3:11]

Participants

8

Reactant 5

HCID 6115AnilineHCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 5460307FumarateHCID 20542261HCID 20542261, compound

Product 1

HCID 12952954HCID 12952954, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

To 8.0 g (0.045 mole) of 4-(2-chloroethyl)-1,3-dimethyl-2-oxo-imidazolidine was added 50 ml of phosphorus oxychloride, and the solution was refluxed for 18 hours, and concentrated in vacuo. The residue was dissolved in 25 ml of methylene chloride and added dropwise to 4.2 g (0.045 mole) of aniline stirring at room temperature. Stirring was continued for two hours. The solution was diluted with chloroform and washed with dilute sodium hydroxide solution. The chloroform was dried, filtered and concentrated in vacuo. The residue was dissolved in isopropyl alcohol and treated with 5.2 g. (0.045 mole) fumaric acid, and the resulting fumarate was recrystallized from isopropyl alcohol and weighed 9.0 g (50% yield); m.p. 109°-112° C.

Workup

  1. temperaturethe solution was refluxed for 18 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in 25 ml of methylene chloride
  4. washwashed with dilute sodium hydroxide solution
  5. dry with materialThe chloroform was dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in isopropyl alcohol
  9. additiontreated with 5.2 g

Sources & evidence

ORD record
ord-a0ca8eb25b804220928d74e12d7f6c25
Source dataset
uspto-grants-1981_01
Patent number
US04247705

Reaction notes

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