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 2352158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2352158
[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

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ef0dd239be2f47e4a5ef1cb6a0ed9ed3
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04876254

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