Water → HCID 13206634, compound

HRID 620394Notes

Reaction equation

HRID 620394 reaction equation
C(N(CC)CC)C.[NH:8]=[C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]=[CH:10]1.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23].O>C(Cl)Cl>[C:21]([N:8]=[C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:11]=[CH:10]1)(=[O:25])[C:22]([CH3:24])=[CH2:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 13206624HCID 13206624, compound

Product 1

HCID 13206634HCID 13206634, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

24.0 g (237 millimoles) of triethylamine were added dropwise to 15.0 g (72.2 millimoles) of 1,4-dihydro-4-imino-1-phenylpyridazine hydrochloricde and 12.8 g (~98 millimols) of ~80% strength methacryloyl chloride in 200 ml of methylene chloride at room temperature, while stirring. After the addition was complete, stirring was continued for a further 2 hours at room temperature, after which water was added to the reaction mixture. The organic phase was separated off, washed with water and evaporated down. The residue was recrystallized three times from toluene. 3.6 g (21% of theory) of 1,4-dihydro-4-methacryloylimino-1-phenylpyridazine were isolated as yellow crystals of melting point 136° C.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. customThe organic phase was separated off
  4. washwashed with water
  5. customevaporated down
  6. customThe residue was recrystallized three times from toluene

Sources & evidence

ORD record
ord-b15c66197a3e4ad2b7d9bb46376ba725
Source dataset
uspto-grants-1989_04
Patent number
US04820821

Reaction notes

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