Phosgene → N-(5-chloropyrid-2-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 1607229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1607229
C(Cl)(Cl)=O.Cl.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:19]([O:21][CH3:22])=[O:20])([CH3:18])[CH2:16][NH:15][N:14]=2)=[CH:9][CH:8]=1.[C:23](Cl)(=[O:25])[NH2:24].N[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=1>C(OCC)(=O)C.C(N(CC)CC)C.C(#N)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([NH:24][C:23]([N:15]2[CH2:16][C:17]([C:19]([O:21][CH3:22])=[O:20])([CH3:18])[C:13]([C:10]3[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=3)=[N:14]2)=[O:25])=[N:29][CH:30]=1

Komponenten

8

Edukt 4

HCID 6371PhosgeneHCID 661742-Amino-5-chloropyridineHCID 68048Carbamic chlorideHCID 198521223-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride

Produkt 1

HCID 19852657N-(5-chloropyrid-2-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittel2×HCID 8471TriethylamineLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 10 ml of acetonitrile containing 4.5 ml of 2.5M phosgene in ethyl acetate was added a slurry of 2.9 g (10 mmole) of 3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride 2.0 g (20 mmole) of triethylamine and 20 ml of acetonitrile. After stirring for 10 minutes the carbamoyl chloride was judged to have been formed and then 1.5 g (11 mmole) of 2-amino-5-chloropyridine was added with an additional 2 g of triethylamine. After stirring for 18 hours the mixture was partitioned between ether and water, washed with brine, dried over magnesium sulfate, filtered concentrated, and chromatographed yielding N-(5-chloropyrid-2-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide, mp 130°-146° C. NMR data was consistent with the structure.

Aufarbeitung

  1. customto have been formed
  2. customwas partitioned between ether and water
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-0dbb9f569893467689776ebb88e09f1d
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04863947

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