Dimethylamine → Dimethyl 1-(4-Chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxamide

HRID 67264

Reaction equation

HRID 67264 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C:10]([C:16]([OH:18])=O)=[N:9]2)=[CH:4][CH:3]=1.[CH2:19]([N:21](CC)[CH2:22]C)C.ClC(OCC)=O.CNC.[OH-].[Na+]>C1(C)C=CC=CC=1.CO.Cl.O>[CH3:19][N:21]([CH3:22])[C:16]([C:10]1[C:11](=[O:15])[CH:12]=[C:13]([CH3:14])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1)=[O:18]

Participants

10

Reactant 5

HCID 674DimethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 197225Fenridazon

Product 1

HCID 13084121Dimethyl 1-(4-Chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxamideYield 49.7%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To an ice cooled suspension of 2.65 g (0.01 mol) 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic Acid (see Example 12) and 1.01 g (0.01 mol) of triethylamine in 50 ml of toluene there is added dropwise 1.09 g (0.01 mol) of ethyl chloroformate. The mixture is stirred at room temperature for 15 min. and is cooled to 5° C. To the mixture there is added 3.375 g (0.03 mol) of 40% dimethylamine (aqueous). The solution formed is stirred at room temperature for 18 hrs. and to it there is added 100 ml of water. The mixture is stirred at room temperature for 1 hr. and the aqueous layer is isolated. The aqueous layer is made basic with 50% sodium hydroxide and extracted with toluene. The toluene extract is dried over magnesium sulfate and concentrated in vacuo to afford 1.8 g of colorless tar. The tar is dissolved in 30 ml of methanol, saturated with anhydrous hydrogen chloride and concentrated in vacuo. The concentrate is slurried in 100 ml of ether for 1 hr. and vacuum filtered. The filter cake is air dried to afford 1.45 g (44% yield) of product, mp 125°-135° C. decomp.

Workup

  1. temperatureis cooled to 5° C
  2. customThe solution formed
  3. stirringis stirred at room temperature for 18 hrs
  4. stirringThe mixture is stirred at room temperature for 1 hr
  5. customand the aqueous layer is isolated
  6. extractionextracted with toluene
  7. extractionThe toluene extract
  8. dry with materialis dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto afford 1.8 g of colorless tar
  11. concentrationconcentrated in vacuo
  12. waitThe concentrate is slurried in 100 ml of ether for 1 hr
  13. filtrationand vacuum filtered
  14. customdried

Sources & evidence

ORD record
ord-e7436b2438204a338c6f8c00e0ebca37
Source dataset
uspto-grants-1982_08
Patent number
US04345934

Linked notes

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