Hydrochloric Acid → HCID 13132150, compound

HRID 2412368Notes

Reaction equation

HRID 2412368 reaction equation
[CH3:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][N:10]=[C:11]1[C:15](=O)[O:14][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:12]1.[NH4+:23].[OH-].Cl>CC(C)=O>[CH3:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:12][C:11]([C:15]([NH2:23])=[O:14])=[N:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 178427908HCID 178427908, compound

Product 1

HCID 13132150HCID 13132150, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.2 g (0.019 mole) of 4-(2-methyl-3-chlorophenylhydrazono)-2-phenyl-oxazoline-5-one (R1 =2--CH3, R2 =3--Cl and R3 =H in the formula II) was added to 60 ml of acetone with stirring. To the resulting mixture, 3 ml of 29% solution of NH4OH (0.024 mole) was added dropwise at room temperature. Then the mixture was refluxed for 25 minutes and heating was stopped. After 3 ml of concentrated hydrochloric acid was added dropwise, and then the mixture was refluxed again for 5 minutes. The obtained reaction mixture was filtered while hot, and 80 ml of water was added to the filtrate. The obtained mixture was allowed to stand for cooling to obtain a product. The product was filtered out, washed with acetone containing water and dried. The crystal was recrystallized from 60 ml of ethanol to obtain 4.8 g of almost colorless crystal, m.p. 198°-200° C., with a yield of 78.2%.

Workup

  1. temperatureThen the mixture was refluxed for 25 minutes
  2. temperatureheating
  3. temperaturethe mixture was refluxed again for 5 minutes
  4. customThe obtained reaction mixture
  5. filtrationwas filtered while hot, and 80 ml of water
  6. additionwas added to the filtrate
  7. temperaturefor cooling
  8. customto obtain a product
  9. filtrationThe product was filtered out
  10. washwashed with acetone
  11. additioncontaining water
  12. customdried
  13. customThe crystal was recrystallized from 60 ml of ethanol
  14. customto obtain 4.8 g of almost colorless crystal, m.p. 198°-200° C.

Sources & evidence

ORD record
ord-25834143da6147eb83743e11ad7d0b77
Source dataset
uspto-grants-1985_01
Patent number
US04492597

Reaction notes

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