Hexane, 1,6-diisocyanato-2,4,4-trimethyl- → 1,6-Bis(7-methylene-1,5-dithiacyclooctan-3-yl)-2,4,4-trimethylhexane dicarbamate

HRID 1364961

Reaktionsgleichung

Reaktionsgleichung von HRID 1364961
[CH2:1]=[C:2]1[CH2:9][S:8][CH2:7][CH:6]([OH:10])[CH2:5][S:4][CH2:3]1.[CH3:11][CH:12]([CH2:17][C:18]([CH3:25])([CH3:24])[CH2:19][CH2:20][N:21]=[C:22]=[O:23])[CH2:13]N=C=O.CC[O:28][CH2:29][CH3:30].C(Cl)Cl>O1CCCC1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>[C:22](=[O:23])([OH:10])[NH2:21].[C:22](=[O:23])([OH:28])[NH2:21].[CH2:1]=[C:2]1[CH2:9][S:8][CH2:7][CH:6]([CH2:11][CH:12]([CH3:13])[CH2:17][C:18]([CH3:25])([CH3:24])[CH2:19][CH2:20][CH:2]2[CH2:9][S:8][CH2:7][C:29](=[CH2:30])[CH2:5][S:4][CH2:3]2)[CH2:5][S:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 61807Hexane, 1,6-diisocyanato-2,4,4-trimethyl-HCID 21881112Ethyl ether methylene chlorideHCID 229467617-Methylene-1,5-dithiocane-3-ol

Produkt 1

HCID 1317287001,6-Bis(7-methylene-1,5-dithiacyclooctan-3-yl)-2,4,4-trimethylhexane dicarbamateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9809426Di-n-butyldilauryltinKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

7-Methylene-1,5-dithiacyclooctan-3-ol (C-8 Alcohol; 2.9 g, 16 mmole) and dibutyl tin dilaurate (10 mg; Sigma-Aldrich) were dissolved in dry tetrahydrofuran (THF, 10 ml) under nitrogen. The resulting solution was heated to reflux and a solution of 2,4,4-trimethyl-1,6-diisocyanatohexane (1.76 g, 8.2 mmole) in dry THF (10 ml) was added dropwise. The reaction was monitored by thin layer chromatography (ether:methylene chloride 1:1) until the starting C8-Alcohol was consumed. (About 12 hours reaction time.) The solvent was then evaporated to give a viscous clear oil/gum. The oil/gum was purified by dissolving in methanol (15 ml per gram) to give a slightly milky solution. A small quantity of the gum separated. The solution was filtered into another flask and water (3 ml per gram) was added slowly to the filtrate with stirring. During the addition, a white residual material separated from the solution. The liquid solvent was decanted and the residue was washed with methanol:water 3.5:1. The washed residue was dissolved in methylene chloride, BHT inhibitor was added (1 mg per gram), and the solution dried with sodium sulfate. The solvent was evaporated to give a slightly cloudy viscous liquid (4.36 g, 96% yield). The product structure of C-8 Diurethane was confirmed by 1H and 13C NMR.

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. customwas consumed
  4. custom(About 12 hours reaction time.) The solvent
  5. customwas then evaporated
  6. customto give a viscous clear oil/gum
  7. customThe oil/gum was purified
  8. dissolutionby dissolving in methanol (15 ml per gram)
  9. customto give a slightly milky solution
  10. customA small quantity of the gum separated
  11. filtrationThe solution was filtered into another flask
  12. additionwater (3 ml per gram) was added slowly to the filtrate
  13. additionDuring the addition
  14. customa white residual material separated from the solution
  15. customThe liquid solvent was decanted
  16. washthe residue was washed with methanol:water 3.5:1
  17. dissolutionThe washed residue was dissolved in methylene chloride
  18. additionBHT inhibitor was added (1 mg per gram)
  19. dry with materialthe solution dried with sodium sulfate
  20. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-410c28cc2f87482b80b215de592c86bb
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888400B2

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