Phenylhydrazine hydrochloride → HCID 178478212, compound

HRID 1578360Notes

Reaction equation

HRID 1578360 reaction equation
[C:1]1(O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]=1.COC.[ClH:12].[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[ClH:12].[C:13]1([NH:19][N:20]=[C:1]2[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 178499087HCID 178499087, compound

Product 1

HCID 178478212HCID 178478212, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

127 G (1 mole) of caprolactim-methyl-ether were added dropwise over the course of 30 minutes to a mixture of 144.5 g (1 mole) of phenylhydrazine hydrochloride and 700 ml of anhydrous ethanol at -10°C, while stirring well and cooling; the mixture was kept for a further hour at -10°C, then for 2 hours at room temperature and for 30 minutes at the reflux temperature. After cooling, the mixture was filtered and further crystal fractions were isolated by concentrating the mother liquor under reduced pressure. Recrystallization from 5 parts of ethanol yielded 220 g (92% of theory) of caprolactam-phenylhydrazone hydrochloride as almost colorless crystals of melting point 244° to 246°C (with decomposition).

Workup

  1. temperaturecooling
  2. waitthe mixture was kept for a further hour at -10°C
  3. waitfor 30 minutes at the reflux temperature
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered
  6. customfurther crystal fractions were isolated
  7. concentrationby concentrating the mother liquor under reduced pressure
  8. customRecrystallization from 5 parts of ethanol

Sources & evidence

ORD record
ord-2028e9cf9bb540e88ad093af4526bea8
Source dataset
uspto-grants-1976_02
Patent number
US03936444

Reaction notes

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