Dimethylformamide → HCID 54123359, compound

HRID 2166337

Reaction equation

HRID 2166337 reaction equation
[Cl:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl:21][CH:22]=[C:23]([Cl:26])[CH2:24]Cl>O>[Cl:1][C:2]1[C:3](=[O:9])[N:4]([CH2:24][C:23]([Cl:26])=[CH:22][Cl:21])[N:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72861,2,3-Trichloro-1-propeneHCID 11430Potassium CarbonateHCID 732474,5-Dichloro-3-hydroxypyridazine

Product 1

HCID 54123359HCID 54123359, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 10.8 g of 4,5-dichloro-3(2H)-pyridazinone and 9.5 g of anhydrous potassium carbonate were added 65 ml of N,N-dimethylformamide and stirred for 10 minutes at room temperature. Then, 10.0 g of 1,2,3-trichloro-1-propene (mixture of E-from and Z-form) were added to the mixture solution and were stirred for 6 hours at 40° C. The solution was poured into a large quantity of water and extracted with benzene, and freed of solvent by distillation under reduced pressure to give 6.0 g of the intended compound (mixture of E-form and Z-form). The compound thus obtained was separated into isomer (m.p.: 93.7°-94.6° C., 112.8°-114.8° C.) by means of column chromatography (on silica gel, eluting with benzene).

Workup

  1. stirringwere stirred for 6 hours at 40° C
  2. extractionextracted with benzene
  3. distillationfreed of solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-37d2610ee48648fcb89c2630c3c8ed70
Source dataset
uspto-grants-1990_07
Patent number
US04945091

Linked notes

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