Hydrochloric Acid → 65884-03-9

HRID 1439617Notes

Reaction equation

HRID 1439617 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C([O-])(=O)C.[Na+].Cl.Cl.[Cl:18][CH:19]([CH3:33])[CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.Cl>C(O)C.C(Cl)(Cl)Cl.O>[ClH:18].[CH3:33][CH:19]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])[CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6942AnthranilamideHCID 517045Sodium AcetateHCID 20338676HCID 20338676, compound

Product 1

HCID 305017365884-03-9

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 75 g. 2-aminobenzamide, 138 g. sodium acetate, 174 g. 1-(2-chloropropyl)-4-phenylpiperazine dihydrochloride, and 455 ml. water was refluxed 4 hours and left overnight at room temperature. Chloroform (200 ml.) was added, the mixture stirred, then filtered. The solid was washed with chloroform which dissolved most of it. The chloroform was separated, the aqueous layer washed with chloroform. The combined chloroform extracts were washed with water, dried, and concentrated to dryness. The residue was recrystallized from 1800 ml. ethanol and again from 2200 ml. ethanol to give 26.3 g., m. 197-8° . A 3rd recrystallization from 1600 ml. ethanol gave 22.4 g. m. 196-8.5° . A 10 g. portion of this was suspended in 100 ml. 95% ethanol, heated to near reflux and 15 ml. 10% hydrochloric acid added. The mixture was cooled with stirring and the solid filtered, washed with ethanol, and dried over P2O5 under vacuum to give 10.8 g., m. 274-81° (dec.)

Workup

  1. additionA mixture of 75 g
  2. filtrationfiltered
  3. washThe solid was washed with chloroform which
  4. dissolutiondissolved most of it
  5. customThe chloroform was separated
  6. washthe aqueous layer washed with chloroform
  7. washThe combined chloroform extracts were washed with water
  8. customdried
  9. concentrationconcentrated to dryness
  10. customThe residue was recrystallized from 1800 ml
  11. customethanol to give 26.3 g
  12. custom197-8°
  13. customA 3rd recrystallization from 1600 ml
  14. customethanol gave 22.4 g
  15. custom196-8.5°
  16. temperatureto near reflux
  17. temperatureThe mixture was cooled
  18. stirringwith stirring
  19. filtrationthe solid filtered
  20. washwashed with ethanol
  21. dry with materialdried over P2O5 under vacuum
  22. customto give 10.8 g

Sources & evidence

ORD record
ord-25616fef822c42079f5580ad725146c4
Source dataset
uspto-grants-1977_11
Patent number
US04060526

Reaction notes

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