Hydrochloric Acid → 1-(2-Nicotinoyl-1-methylvinylamino)-3-(p-cylcohexylureidophenoxy)-propan-2-ol

HRID 372112

Reaktionsgleichung

Reaktionsgleichung von HRID 372112
[CH:1]1([NH:7][C:8](=[O:22])[NH:9][C:10]2[CH:21]=[CH:20][C:13]([O:14][CH2:15][CH:16]([OH:19])[CH2:17][NH2:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl.[C:30]([CH:38]=[C:39](Cl)[CH3:40])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[N:33][CH:32]=1.[Na].C(CC(=O)C)(=O)C1C=CC=NC=1.Cl.S(Cl)(Cl)=O.Cl.C(C(C)=CCl)(=O)C1C=CC=NC=1>C1(C)C=CC=CC=1>[C:30]([CH:38]=[C:39]([NH:18][CH2:17][CH:16]([OH:19])[CH2:15][O:14][C:13]1[CH:20]=[CH:21][C:10]([NH:9][C:8]([NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:22])=[CH:11][CH:12]=1)[CH3:40])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[N:33][CH:32]=1

Komponenten

10

Edukt 8

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 3001601-(Pyridin-3-yl)butane-1,3-dione2×HCID 5360545SodiumHCID 122382301-(p-Cyclohexylureido-phenoxy)-3-amino-propan-2-olHCID 736763322-Nicotinoyl-1-methylvinyl chloride hydrochlorideHCID 131711099Nicotinoyl-methylvinyl chloride hydrochloride

Produkt 1

HCID 706192841-(2-Nicotinoyl-1-methylvinylamino)-3-(p-cylcohexylureidophenoxy)-propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

6.1 g of 1-(p-cyclohexylureido-phenoxy)-3-amino-propan-2-ol ##STR49## are dissolved in 50 ml of anhydrous toluene and 5.7 g of anhydrous potassium carbonate are added. A mixture of 4.4 g of 2-nicotinoyl-1-methylvinyl chloride hydrochloride of the formula ##STR50## (prepared from the sodium salt of nicotinoyl-acetone, which is first converted by means of HCl gas into the hydrochloride of free nicotinoyl-acetone and then, using thionyl chloride, into nicotinoyl-methylvinyl chloride hydrochloride) in 50 ml of anhydrous toluene is added slowly, with cooling and stirring, to this mixture and stirring is subsequently continued for 36 hours at room temperature. The product is then filtered and the residue is dissolved in water and the solution is rendered alkaline by means of sodium carbonate and extracted three times with chloroform. The chloroform extracts are concentrated, together with the original toluene filtrate, in vacuo at approx. 14 to 20 mm Hg. 1-(2-Nicotinoyl-1-methylvinylamino)-3-(p-cylcohexylureidophenoxy)-propan-2-ol is thus obtained after repeated recrystallisation from aqueous ethanol. ##STR51## Melting point: 168° C Analysis: (C25H32N4O4)

Aufarbeitung

  1. temperaturewith cooling
  2. stirringstirring
  3. filtrationThe product is then filtered
  4. dissolutionthe residue is dissolved in water
  5. extractionextracted three times with chloroform
  6. concentrationThe chloroform extracts are concentrated, together with the original toluene filtrate, in vacuo at approx. 14 to 20 mm Hg

Quellen und Nachweise

ORD-Eintrag
ord-735257e6624e41b3a249a3dcce972318
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04088764

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