4,5-Dihydro-2-thiazolamine → 4-[(4,5-dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis(phenylmethylene)-2H-thiopyran-4-ol

HRID 65662

Reaktionsgleichung

Reaktionsgleichung von HRID 65662
[C:1]1([CH:7]=[C:8]2[C:13](=[O:14])[C:12](=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][S:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][C:23]1[S:24][CH2:25][CH2:26][N:27]=1>CC(C)=O>[S:24]1[CH2:25][CH2:26][N:27]=[C:23]1[NH:22][C:13]1([OH:14])[C:8](=[CH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][S:10][CH2:11][C:12]1=[CH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 156894,5-Dihydro-2-thiazolamine2×HCID 336779tetrahydro-3,5-bis(phenylmethylene)-4H-thiopyran-4-one

Produkt 1

HCID 543093604-[(4,5-dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis(phenylmethylene)-2H-thiopyran-4-olAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel3×

Versuchsvorschrift

A slurry of tetrahydro-3,5-bis-(phenylmethylene)-4H-thiopyran-4-one (5.5 g, 18.9 mmole) in 200 ml of acetone is treated with a solution of 2-amino-2-thiazoline (2.0 g, 19.6 mmole, filtered) in 100 ml of acetone at room temperature. The mixture never becomes homogeneous, but the nature of the solids change (yellow to white). After stirring at room temperature for 2 days, the starting ketone remains as evidenced by tlc. Additional 2-amino-2-thiazoline (1 g, 9.8 mmole, filtered) in 50 ml of acetone is added and the mixture is heated at reflux temperature for 1 day. Upon cooling to room temperature, filtration and washing with acetone affords a combined yield of 6.9 g (92.5%) of product in two crops, m.p. 171°-172.5°).

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux temperature for 1 day
  3. temperatureUpon cooling to room temperature
  4. filtrationfiltration
  5. washwashing with acetone

Quellen und Nachweise

ORD-Eintrag
ord-aaf3d8cc1bea45509c5acd085d8e0556
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04128647

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