Hydroquinone → 3-(4-Chlorophenyl)-7-[(4-chlorophenyl)methylene]-2,3,3a,4,6,7-hexahydro-2-propylthiopyrano[4,3-c]pyrazole

HRID 1576017

Reaktionsgleichung

Reaktionsgleichung von HRID 1576017
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[C:14](=O)[C:13](=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:12][S:11][CH2:10]2)=[CH:4][CH:3]=1.[CH2:24]([NH:27][NH2:28])[CH2:25][CH3:26].C1(C=CC(O)=CC=1)O>ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:27]([CH2:24][CH2:25][CH3:26])[N:28]=[C:14]3[C:13](=[CH:16][C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)[CH2:12][S:11][CH2:10][CH:9]23)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 785HydroquinoneHCID 42007Hydrazine, propyl-HCID 3824694H-Thiopyran-4-one, 3,5-bis[(4-chlorophenyl)methylene]tetrahydro-

Produkt 1

HCID 536504893-(4-Chlorophenyl)-7-[(4-chlorophenyl)methylene]-2,3,3a,4,6,7-hexahydro-2-propylthiopyrano[4,3-c]pyrazoleAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

A mixture of 6.0g of tetrahydro-3,5-bis-[(4-chlorophenyl)methylene]-4H-thiopyran-4-one, 1.3g of n-propyl hydrazine, and 100mg of hydroquinone in 100ml of dichloroethane is heated at reflux temperature for 2.5 hours and allowed to cool to room temperature. The reaction mixture is washed with dilute hydrochloric acid and water, and then dried over calcium chloride. After the solvent is removed in vacuo, the residue is chromatographed on a dry packed neutral alumina column (Activity I). The fractions eluted with 0-5% ethyl acetate/hexane are combined and crystallized from acetone/acetonitrile to give 2.8g of the title compound, melting point 118°-122°C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperature for 2.5 hours
  3. washThe reaction mixture is washed with dilute hydrochloric acid and water
  4. dry with materialdried over calcium chloride
  5. customAfter the solvent is removed in vacuo
  6. customthe residue is chromatographed on a dry
  7. washThe fractions eluted with 0-5% ethyl acetate/hexane
  8. customcrystallized from acetone/acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-b7b880a812034aebbe379598b6672279
Quelldatensatz
uspto-grants-1976_09
Patentnummer
US03979381

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