Hydrochloric Acid → HCID 13132141, compound

HRID 2412367Notes

Reaction equation

HRID 2412367 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[CH3:8].[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[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 178426641HCID 178426641, compound

Product 1

HCID 13132141HCID 13132141, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Three grams (0.01 mole) of 4-(3,4-dimethylphenylhydrazono)-2-phenyl-oxazoline-5-one (R1 =3--CH3, R2 =4--CH3 and R3 =H in the formula II) was suspended in 16 ml of acetone. To the resulting suspension, 1.57 ml of 29% solution of NH4OH (0.013 mole) was added dropwise at room temperature. After refluxing for 25 minutes, heating was stopped and 1.57 ml of concentrated hydrochloric acid was added dropwise. The resulting mixture was again refluxed for 5 minutes. 42 ml of water was then added to the reaction mixture, and obtained crystal was filtered out, washed with acetone containing water and dried. The thus treated crystal was recrystallized from a mixture of 8.8 ml of ethanol and 3 ml of water to obtain 2.25 g of almost colorless crystal, m.p. 169°-170° C., with a yield of 76.9%.

Workup

  1. temperatureAfter refluxing for 25 minutes
  2. temperatureheating
  3. temperatureThe resulting mixture was again refluxed for 5 minutes
  4. customobtained crystal
  5. filtrationwas filtered out
  6. washwashed with acetone
  7. additioncontaining water
  8. customdried
  9. customThe thus treated crystal was recrystallized from a mixture of 8.8 ml of ethanol and 3 ml of water
  10. customto obtain 2.25 g of almost colorless crystal, m.p. 169°-170° C.

Sources & evidence

ORD record
ord-a93dccdefc4245c794c26be2e30eca68
Source dataset
uspto-grants-1985_01
Patent number
US04492597

Reaction notes

Loading…