1,1'-Carbonyldiimidazole → 4-(6-Oxo-1,4,5,6-tetrahydropyridazin-3-yl)benzyl 4-(3-chlorophenyl)-1,4-dihydro-2,6-dimethyl-5-nitropyridine-3-carboxylate

HRID 2352158Notes

Reaction equation

HRID 2352158 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19]([OH:21])=[O:20])[CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[O:34]=[C:35]1[NH:40][N:39]=[C:38]([C:41]2[CH:48]=[CH:47][C:44]([CH2:45]O)=[CH:43][CH:42]=2)[CH2:37][CH2:36]1.C[O-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19]([O:21][CH2:45][C:44]2[CH:43]=[CH:42][C:41]([C:38]3[CH2:37][CH2:36][C:35](=[O:34])[NH:40][N:39]=3)=[CH:48][CH:47]=2)=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 102198804-(6-Oxo-1,4,5,6-tetrahydropyridazin-3-yl)benzyl alcoholHCID 10942334Sodium MethoxideHCID 183182934-(3-Chlorophenyl)-1,4-dihydro-2,6-dimethyl-5-nitropyridine-3-carboxylic acid

Product 1

HCID 142304124-(6-Oxo-1,4,5,6-tetrahydropyridazin-3-yl)benzyl 4-(3-chlorophenyl)-1,4-dihydro-2,6-dimethyl-5-nitropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10 mmol of 4-(3-chlorophenyl)-1,4-dihydro-2,6-dimethyl-5-nitropyridine-3-carboxylic acid are suspended in 40 ml of absolute tetrahydrofuran and treated with 12.5 mmol of carbonyldiimidazole. The suspension is then stirred for 30 minutes at room temperature and for 30 minutes at reflux temperature. A solution of 11 mmol of 4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)benzyl alcohol and 10 mg of sodium methylate in 10 ml of tetrahydrofuran is then added, and the mixture is heated to reflux for 3.5 hours. It is then evaporated, and the residue is taken up in methylene chloride, washed successively with 1N hydrochloric acid, 1N sodium hydroxide solution and water, dried with magnesium sulphate and evaporated. The residue crystallizes from a little i-propanol.

Workup

  1. temperatureat reflux temperature
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 3.5 hours
  4. customIt is then evaporated
  5. washwashed successively with 1N hydrochloric acid, 1N sodium hydroxide solution and water
  6. dry with materialdried with magnesium sulphate
  7. customevaporated
  8. customThe residue crystallizes from a little i-propanol

Sources & evidence

ORD record
ord-ef0dd239be2f47e4a5ef1cb6a0ed9ed3
Source dataset
uspto-grants-1989_10
Patent number
US04876254

Reaction notes

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