Dicyclohexylcarbodiimide → 4,4-Dimethyl-9-[4-(thiomorpholino)butyryloxy]-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[c][1]benzopyran hydrochloride

HRID 267350

Reaktionsgleichung

Reaktionsgleichung von HRID 267350
[CH3:1][C:2]1([CH3:25])[C:7]2[CH2:8][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.[ClH:26].[S:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][C:36](O)=[O:37])[CH2:29][CH2:28]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:26].[CH3:25][C:2]1([CH3:1])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([O:24][C:36](=[O:37])[CH2:35][CH2:34][CH2:33][N:30]3[CH2:29][CH2:28][S:27][CH2:32][CH2:31]3)=[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

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 215348Cyclopenta(c)(1)benzopyran-9-ol, 1,2,3,4-tetrahydro-4,4-dimethyl-7-(1,2-dimethylheptyl)-HCID 70633382gamma-Thiomorpholinobutyric acid hydrochloride

Produkt 1

HCID 681357664,4-Dimethyl-9-[4-(thiomorpholino)butyryloxy]-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[c][1]benzopyran hydrochlorideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1.5 g. (4.4 mmole) of 4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[ c][1]benzopyran, 0.99 g. (4.4 mmole) of γ-thiomorpholinobutyric acid hydrochloride, and 0.99 g. (4.8 mmole) of dicyclohexylcarbodiimide in 125 ml. of methylene chloride was stirred and heated at reflux for 16 hours. The reaction mixture was cooled and the byproduct of dicyclohexylurea was removed by suction filtration. The solvents were evaporated to give a residue which crystallized from a mixture of 10 ml. chloroform/40 ml. diethyl ether to give 0.85 g. (35%) of the desired product as a beige solid, m.p. 167°-171°C. The material was pure by thin layer chromatography, and the infrared and nuclear magnetic resonance spectra were in agreement with the proposed structure.

Aufarbeitung

  1. additionA mixture of 1.5 g
  2. temperatureheated
  3. temperatureat reflux for 16 hours
  4. temperatureThe reaction mixture was cooled
  5. customthe byproduct of dicyclohexylurea was removed by suction filtration
  6. customThe solvents were evaporated
  7. customto give a residue which
  8. customcrystallized from a mixture of 10 ml
  9. customdiethyl ether to give 0.85 g

Quellen und Nachweise

ORD-Eintrag
ord-848c5b9b4e2c419684df6ef0e345a49a
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03941782

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