Hydrochloric Acid → HCID 178478546, compound

HRID 1578357Notes

Reaction equation

HRID 1578357 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[C:11]1(O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]=1.COC>CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][N:10]=[C:11]2[NH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 75332(3-Chlorophenyl)hydrazineHCID 178499087HCID 178499087, compound

Product 1

HCID 178478546HCID 178478546, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

300 G of hydrogen chloride gas were introduced into a solution of 1,000g(7 moles) of 3-chlorophenylhydrazine and 980 g (7.7 moles) of caprolactim-methyl-ether in 4,000 ml of methanol at 10° to 20°C while stirring and cooling with an ice bath, and the reaction mixture was kept for a further hour at 20°C, raised to the reflux temperature and kept at 65°C for 11/2 hours. After cooling, the crystals which had separated out were filtered off and further crystal fractions were isolated by concentrating the mother liquors under reduced pressure. After recrystallization from 2 parts of methanol, 1,845 g (96% of theory) of caprolactam-(3-chlorophenylhydrazone) hydrochloride were obtained as colorless crystals of melting point 280° to 282°C.

Workup

  1. temperaturecooling with an ice bath
  2. waitthe reaction mixture was kept for a further hour at 20°C
  3. temperatureraised to the reflux temperature
  4. customkept at 65°C for 11
  5. custom2 hours
  6. temperatureAfter cooling
  7. customthe crystals which had separated out
  8. filtrationwere filtered off
  9. customfurther crystal fractions were isolated
  10. concentrationby concentrating the mother liquors under reduced pressure
  11. customAfter recrystallization from 2 parts of methanol

Sources & evidence

ORD record
ord-aa42e09049d34b40ac97a7098e9e2b8f
Source dataset
uspto-grants-1976_02
Patent number
US03936444

Reaction notes

Loading…