2-Benzothiazolinone, hydrazone → 1-(2-Benzothiazolyl)-5-(4-chlorophenyl)-5-hydroxy-3-(3-hydroxypropyl)-2-pyrazoline

HRID 5013

Reaktionsgleichung

Reaktionsgleichung von HRID 5013
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][OH:14])=[CH:4][CH:3]=1.[NH:17]([C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1)[NH2:18]>N1C=CC=CC=1.CO>[S:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[N:17]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:16])[CH2:9][C:10]([CH2:11][CH2:12][CH2:13][OH:14])=[N:18]1

Komponenten

5

Edukt 2

HCID 119882-Benzothiazolinone, hydrazoneHCID 144974141-(4-Chlorophenyl)-6-hydroxyhexan-1,3-dione

Produkt 1

HCID 197975731-(2-Benzothiazolyl)-5-(4-chlorophenyl)-5-hydroxy-3-(3-hydroxypropyl)-2-pyrazoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

6-(4-Chlorophenyl)-4,6-diketohexanol (7.2 g, 30 mM) was treated with 2-hydrazinobenzothiazole (4.96 g, 30 mM) in pyridine (5 ml) and MeOH (150 ml) at reflux for 2 hr and then allowed to stand at RT for 48 hr. The solvents were removed in vacuo and the crude residue purified by flash chromatography on silica with Et2O:Et3N (2.5%) as eluent. The title compound (1) was obtained as a pale yellow solid, (3.15 g, mp=132°-134° C.) upon recrystallization from Et2O:hexane. NMR(CDCl3) δ 3.2 (2H, C4 -H); MS, m/e 387 (M+).

Aufarbeitung

  1. temperatureat reflux for 2 hr
  2. customThe solvents were removed in vacuo
  3. customthe crude residue purified by flash chromatography on silica with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-049f17bf09a5437991fcb4535a89d071
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242940

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