Hydrochloric Acid → HCID 13132156, compound

HRID 2412369Notes

Reaction equation

HRID 2412369 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][N:10]=[C:11]2[C:15](=O)[O:14][C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:12]2)[CH:5]=[CH:6][C:7]=1[F:8].[NH4+:23].[OH-].Cl.O>CC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:12][C:11]([C:15]([NH2:23])=[O:14])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 178428698HCID 178428698, compound

Product 1

HCID 13132156HCID 13132156, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.0 g (0.01 mole) of 4-(3-methyl-4-fluorophenylhydrazono)-2-phenyl-oxazoline-5-one (R1 =3--CH3, R2 =4--F and R3 =H in the formula II) was suspended in 16 ml of acetone. To the suspension, 1.57 ml of 29% solution of NH4OH (0.013 mole) was added dropwise at room temperature. After refluxing the reaction mixture for 25 minutes, heating was stopped and 1.57 ml of concentrated hydrochloric acid was added dropwise. After the addition was over, the reaction mixture was refluxed again for 5 minutes. Then 40 ml of water was added to the reaction mixture, and the resulting crystal was filtered out, washed with acetone containing water and dried. The obtained crystal was recrystallized from a mixture of 20 ml of ethanol and 5 ml of water to obtain 1.7 g of almost colorless crystal, m.p. 123°-126° C., with a yield of 55.2%.

Workup

  1. temperatureAfter refluxing the reaction mixture for 25 minutes
  2. temperatureheating
  3. additionAfter the addition
  4. temperaturewas refluxed again for 5 minutes
  5. filtrationthe resulting crystal was filtered out
  6. washwashed with acetone
  7. additioncontaining water
  8. customdried
  9. customThe obtained crystal was recrystallized from a mixture of 20 ml of ethanol and 5 ml of water
  10. customto obtain 1.7 g of almost colorless crystal, m.p. 123°-126° C.

Sources & evidence

ORD record
ord-f1734e565fd54ffbacee4753ebc3d2b8
Source dataset
uspto-grants-1985_01
Patent number
US04492597

Reaction notes

Loading…