Citric Acid → HCID 86746365, Verbindung

HRID 373856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373856
N[C:2]1([C:21](=[O:34])[CH:22]([C:32]#[N:33])[C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:24])[NH:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]2[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[S:15][CH2:16][C:3]1=2.N1C=CC=[CH:37][CH:36]=1.C(O)(=O)C[C:43](CC(O)=O)([C:45]([OH:47])=[O:46])[OH:44].C[N:55](C)C=O>>[C:32]([CH:22]([C:21]([C:2]1[C:3]2[CH2:16][S:15][C:14]3[CH:17]=[CH:18][C:19]([NH:55][C:43]([C:45]([O:47][CH2:36][CH3:37])=[O:46])=[O:44])=[CH:20][C:13]=3[C:4]=2[N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1)=[O:34])[C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24])#[N:33]

Komponenten

5

Edukt 4

HCID 311Citric AcidHCID 1049PyridineHCID 6228DimethylformamideHCID 86746366HCID 86746366, Verbindung

Produkt 1

HCID 86746365HCID 86746365, Verbindung

Versuchsvorschrift

3-(3-Amino-1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl)-2-cyano-3-oxo-N-phenyl-propanamide (1.2 g) dissolved in anhydrous dimethylformamide (70 ml) containing pyridine (1 ml) is reacted with ethyl oxalyl chloride (0.7 g) under stirring at room temperature for 6 hours. The reaction mixture is diluted with ice water and acidified to pH 4 with citric acid. The precipitate is filtered and washed with water. Crystallization from CHCl3 /ethanol yields 1.2 g of 2-cyano-3-(8-ethoxalylamino-1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide, m.p. 273°-277° C.

Aufarbeitung

  1. filtrationThe precipitate is filtered
  2. washwashed with water
  3. customCrystallization from CHCl3 /ethanol

Quellen und Nachweise

ORD-Eintrag
ord-05dae74833ce4de28239e2c96ab3c4f6
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166152

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