2-Methyl-2-thiopseudourea sulfate → HCID 13457210, Verbindung

HRID 2290321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2290321
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][C:22]([NH:24][NH2:25])=O)=[C:9]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].S(O)(O)(=O)=O.CS[C:38](=[NH:40])[NH2:39].N12CCCC1=NCCC2>C(O)CCC>[NH2:40][C:38]1[N:39]=[C:22]([CH2:21][O:20][CH2:19][C:10]2[NH:11][C:12]([CH3:18])=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:9]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[NH:24][N:25]=1

Komponenten

5

Edukt 3

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 70044597HCID 70044597, Verbindung

Produkt 1

HCID 13457210HCID 13457210, VerbindungAusbeute 15,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A solution of 2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}-acetylhydrazine (0.87 g), 2-methylisothiourea sulphate (0.68 g) and 1,5-diazabicyclo[4.3.0]non-5-ene (0.74 g) in n-butanol (30 ml) was heated under reflux for 16 hours and then evaporated. The residue was partitioned between dichloromethane and water and the organic layer dried (Na2SO4) and evaporated. The residual oil was purified by chromatography on silica (t.l.c. grade, 10 g) using dichloromethane plus 0-100% v/v ethyl acetate as eluant. Appropriate fractions were combined and evaporated and the residual oil triturated with ethyl acetate. The resulting solid was collected, washed with ethyl acetate and dried to give the title compound (0.14 g), m.p. 199°-202° C. decomp.

Aufarbeitung

  1. temperatureunder reflux for 16 hours
  2. customevaporated
  3. customThe residue was partitioned between dichloromethane and water
  4. dry with materialthe organic layer dried (Na2SO4)
  5. customevaporated
  6. customThe residual oil was purified by chromatography on silica (t.l.c. grade, 10 g)
  7. customevaporated
  8. customthe residual oil triturated with ethyl acetate
  9. customThe resulting solid was collected
  10. washwashed with ethyl acetate
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-cd84fbe6218545f09419eaf47065d42b
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04616024

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