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Dicyclohexylcarbodiimide → 9-[4-(Diethylamino)butyryloxy]-1,2-dihydro-4,4-dimethyl-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran hydrochloride

HRID 1579099
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Reaktionsgleichung

Reaktionsgleichung von HRID 1579099
[CH3:1][C:2]1([CH3:25])[C:7]2[S:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:24])=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[ClH:41].[CH2:42]([N:44]([CH2:51][CH3:52])[CH2:45][CH2:46][CH2:47][C:48](O)=[O:49])[CH3:43]>C(Cl)Cl>[ClH:41].[CH2:42]([N:44]([CH2:51][CH3:52])[CH2:45][CH2:46][CH2:47][C:48]([O:24][C:11]1[C:5]2[C:6]3[CH2:10][CH2:9][S:8][C:7]=3[C:2]([CH3:1])([CH3:25])[O:3][C:4]=2[CH:14]=[C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])[CH:12]=1)=[O:49])[CH3:43]
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Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 2135232H-Thieno(2,3-c)(1)benzopyran-9-ol, 1,4-dihydro-7-(1,2-dimethylheptyl)-4,4-dimethyl-HCID 137955394-(Diethylamino)butanoic acid hydrochloride

Produkt 1

HCID 215579049-[4-(Diethylamino)butyryloxy]-1,2-dihydro-4,4-dimethyl-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran hydrochlorideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.5 g. (1.39 mmole) of 1,2-dihydro-4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran, 0.31 g. (1.50 mmole; Aldrich Chemical Co.) of dicyclohexylcarbodiimide and 0.272 g. (1.39 mmole) of 4-diethylaminobutyric acid hydrochloride (F. F. Blicke, W. B. Wright, Jr., and M. R. Zienty, J. Amer. Chem. Soc., 63 2488 (1941)) were combined in 30 ml. of methylene chloride and stirred at room temperature for 4 hours. The insoluble by-product of dicyclohexylurea was separated by filtration and the methylene chloride was removed on a rotary evaporator. Attempts to crystallize the material were unsuccessful and 400 mg. (53%) of dark brown residue was obtained. The structure was confirmed by the IR and NMR spectra; and TLC gave Rf 0.5 in 5% MeOH/CHCl3. The acid addition salt may be converted to the free base form by methods well known in the art, and the resulting free base form may then be reacted with another suitable acid to form a different acid addition salt.

Aufarbeitung

  1. customThe insoluble by-product of dicyclohexylurea was separated by filtration
  2. customthe methylene chloride was removed on a rotary evaporator
  3. customto crystallize the material

Quellen und Nachweise

ORD-Eintrag
ord-74df4688fe6b477e9a2eacdf1ef14681
Quelldatensatz
uspto-grants-1976_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03940421

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