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Water → Di-n-butyl 1-(p-Chlorophenyl)-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxamide

HRID 67266
Notes
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Reaction equation

HRID 67266 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.C(N(CC)CC)C.[CH2:26]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH3:29].O>C1(C)C=CC=CC=1>[CH2:26]([N:30]([CH2:31][CH2:32][CH2:33][CH3:34])[C:16]([C:10]1[C:11](=[O:15])[CH:12]=[C:13]([CH3:14])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]=1)=[O:18])[CH2:27][CH2:28][CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8148DibutylamineHCID 8471TriethylamineHCID 197225Fenridazon

Product 1

HCID 13084131Di-n-butyl 1-(p-Chlorophenyl)-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxamideYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent
2×

Procedure

To an ice cooled suspension of 5.29 g (0.02 mol) 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic Acid (see Example 12) and 2.02 g (0.02 mol) of triethylamine in 100 ml of toluene there is added dropwise 2.17 g (0.02 mol) of ethyl chlorofomate. The suspension formed is stirred at room temperature for 15 min. and is cooled to 5° C. To the suspension is added 2.59 g (0.02 mol) di-n-butylamine and the mixture is stirred at room temperature for 18 hrs. To the mixture is added 100 ml of water and the suspension formed is stirred at room temperature for 1 hr. The toluene layer is isolated, dried over magnesium sulfate and concentrated in vacuo. The residue oil is dissolved in 25 ml of ether and to it there is added 25 ml of hexane. The mixture is allowed to stand at room temperature for 30 minutes and is vacuum filtered. The filter cake is washed with hexane and air dried to afford 5.5 g (73% yield) of product, mp 101°-105° C.

Workup

  1. additionthere is added dropwise 2.17 g (0.02 mol) of ethyl chlorofomate
  2. customThe suspension formed
  3. temperatureis cooled to 5° C
  4. stirringthe mixture is stirred at room temperature for 18 hrs
  5. customthe suspension formed
  6. stirringis stirred at room temperature for 1 hr
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue oil is dissolved in 25 ml of ether and to it there
  10. additionis added 25 ml of hexane
  11. waitto stand at room temperature for 30 minutes
  12. filtrationfiltered
  13. washThe filter cake is washed with hexane and air
  14. customdried

Sources & evidence

ORD record
ord-adeb08de34bc457090a8057060728236
Source dataset
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04345934

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes