Cyclohexanol → Cyclohexyl 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylate

HRID 543049Notes

Reaction equation

HRID 543049 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:17])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(O[CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=O.C1(O)CCCCC1>C1(C)C=CC=CC=1.CCCCCC.O>[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]([O:18][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:17])=[N:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 7966CyclohexanolHCID 8471TriethylamineHCID 83262Carbonochloridic acid, cyclohexyl esterHCID 197225Fenridazon

Product 1

HCID 13084122Cyclohexyl 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylateYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent3×HCID 8058HexaneSolvent

Procedure

To an ice cooled suspension of 5.29 g (0.02 mol) 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylic Acid (see Example 12) and 2.02 g (0.02 mol) of triethylamine in 75 ml of toluene there is added 3.25 g (0.02 mol) of cyclohexyl chloroformate. The suspension formed is stirred at room temperature for 15 minutes and to it there is added 3.2 g (0.022 mol) of cyclohexanol in 50 ml of toluene. The mixture is stirred at room temperature for 38 hrs. and to it there is added 100 ml of water. The mixture is stirred at room temperature for 1 hr. and the toluene layer is isolated and poured into 600 ml of hexane. The suspension formed is stirred at room temperature for 1/2 hr. and is vacuum filtered. The filter cake is air dried to afford 4.5 g (65% yield) of product, mp 160°-162° C.

Workup

  1. customThe suspension formed
  2. stirringThe mixture is stirred at room temperature for 38 hrs
  3. stirringThe mixture is stirred at room temperature for 1 hr
  4. customThe suspension formed
  5. stirringis stirred at room temperature for 1/2 hr
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-1d12eefc9fcf4d988436d5edc4c486fe
Source dataset
uspto-grants-1987_04
Patent number
US04661145

Reaction notes

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