Dicyclohexylcarbodiimide → 4-Octyloxyphenyl 2-heptylimidazo[2,1-b]thiazole-6-carboxylate

HRID 1458493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458493
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:23]1[S:27][C:26]2=[N:28][C:29]([C:31]([OH:33])=[O:32])=[CH:30][N:25]2[CH:24]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH2:34]([O:42][C:43]1[CH:48]=[CH:47][C:46](O)=[CH:45][CH:44]=1)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:16]([C:23]1[S:27][C:26]2=[N:28][C:29]([C:31]([O:33][C:46]3[CH:47]=[CH:48][C:43]([O:42][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:44][CH:45]=3)=[O:32])=[CH:30][N:25]2[CH:24]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 77412Phenol, 4-(octyloxy)-HCID 701107392-Heptylimidazo[2,1-b]-thiazole-6-carboxylic acid

Produkt 1

HCID 867534624-Octyloxyphenyl 2-heptylimidazo[2,1-b]thiazole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.2 g of N,N'-dicyclohexylcarbodiimide are added in portions to a solution of 1.3 g of 2-heptylimidazo[2,1-b]-thiazole-6-carboxylic acid, 1 g of 4-octyloxyphenol and 0.1 g of 4-(dimethylamino)pyridine in 25 ml of dichloromethane within 10 minutes while stirring. The mixture is stirred overnight at room temperature and then filtered. The filtrate is diluted with dichloromethane, washed with two portions of 50 ml each of saturated sodium carbonate solution and then with water, dried over magnesium sulphate and filtered, and the filtrate is evaporated. Recrystallization of the residue from ethyl acetate/cyclohexane gives 4-octyloxyphenyl 2-heptylimidazo[2,1-b]thiazole-6-carboxylate, m.p.(C/SA): 112.6° C., c.p.(SA /I): 151.4° C.

Aufarbeitung

  1. stirringThe mixture is stirred overnight at room temperature
  2. filtrationfiltered
  3. additionThe filtrate is diluted with dichloromethane
  4. washwashed with two portions of 50 ml each of saturated sodium carbonate solution
  5. dry with materialwith water, dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe filtrate is evaporated
  8. customRecrystallization of the residue from ethyl acetate/cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-fbd9e94e23914721be1a5ca68e3af958
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05851425

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