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

HRID 67263
Notes
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Reaction equation

HRID 67263 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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-methyl pyridazine-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-1ff062a96b93482eaad2b50dc2687f39
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