Toluene → HCID 13206635, compound

HRID 620397Notes

Reaction equation

HRID 620397 reaction equation
C1(C)C=CC=CC=1.Cl.[NH:9]=[C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=[CH:11]1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>O>[C:22]([N:9]=[C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:12]=[CH:11]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 21246174HCID 21246174, compound

Product 1

HCID 13206635HCID 13206635, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

80 ml of toluene were added to a solution of 10.0 g (48.2 millimoles) of 1,4-dihydro-4-imino-1-phenylpyridazine hydrochloride in 80 ml of water. First 6.8 g (48.4 millimoles) of benzoyl chloride and then, in the course of 15 minutes, 4.0 g (100 millimoles) of NaOH in 20 ml of water were added to the two-phase system at room temperature, whilst stirring, the mixture was stirred for a further hour at room temperature and the product was then filtered off under suction. The solid obtained was washed with water, dried and recrystallized from ethanol. 9.5 g (72% of theory) of 4-benzoylimino-1,4-dihydro-1-phenylpyridazine were isolated as yellow crystals of melting point 175°-176° C.

Workup

  1. stirringthe mixture was stirred for a further hour at room temperature
  2. filtrationthe product was then filtered off under suction
  3. customThe solid obtained
  4. washwas washed with water
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a7fae6f058dd46a79cb1a824bf097894
Source dataset
uspto-grants-1989_04
Patent number
US04820821

Reaction notes

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