Ethanol → 2,3,8,9-Tetrahydro-5-(3,4,5-trimethoxyphenyl)-9-[(3,4,5-trimethoxyphenyl)methylene]-5H,6H-pyrano[4,3-d]thiazolo[3,2-a]pyrimidine

HRID 65673

Reaktionsgleichung

Reaktionsgleichung von HRID 65673
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]2[C:19](=O)[C:18](=[CH:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)[CH2:17][O:16][CH2:15]2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[NH2:34][C:35]1[S:36][CH2:37][CH2:38][N:39]=1.CCO>C(Cl)(Cl)Cl>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([CH:13]2[N:39]3[CH2:38][CH2:37][S:36][C:35]3=[N:34][C:19]3[C:18](=[CH:21][C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)[CH2:17][O:16][CH2:15][C:14]2=3)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 156894,5-Dihydro-2-thiazolamineHCID 2740872Tetrahydro-3,5-bis[(3,4,5-trimethoxyphenyl)methylene]-4H-pyran-4-one

Produkt 1

HCID 217866802,3,8,9-Tetrahydro-5-(3,4,5-trimethoxyphenyl)-9-[(3,4,5-trimethoxyphenyl)methylene]-5H,6H-pyrano[4,3-d]thiazolo[3,2-a]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A stirred solution of tetrahydro-3,5-bis[(3,4,5-trimethoxyphenyl)methylene]-4H-pyran-4-one (3.0 g, 6.5 mmole) and 2-amino-2-thiazoline (0.8 g, 7.8 mmole) in 75 ml of CHCl3 is heated at reflux for 44 hours. After cooling, the solution is filtered to remove a small amount of insoluble material. The solvent is evaporated to give an oily residue which solidifies when treated with a small amount of EtOH. The yield is 2.2 g, m.p. 166°-168°. Crystallization from 10 ml of MeCN gives 1.5 g (42%) of light yellow solid, m.p. 153°-155°. The m.p. of a sample of this material does not change when recrystallized from MeCN.

Aufarbeitung

  1. temperatureat reflux for 44 hours
  2. temperatureAfter cooling
  3. filtrationthe solution is filtered
  4. customto remove a small amount of insoluble material
  5. customThe solvent is evaporated
  6. customto give an oily residue which
  7. customCrystallization from 10 ml of MeCN
  8. customgives 1.5 g (42%) of light yellow solid, m.p. 153°-155°
  9. customrecrystallized from MeCN

Quellen und Nachweise

ORD-Eintrag
ord-21dd2336b8384ddb984830a2611bafb1
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04128648

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