Methanol → Bis [4-(vinyloxy)butyl]trimethyl-1,6-hexanediylbiscarbamate

HRID 643185

反応式

HRID 643185 の反応式
[CH3:1][CH:2]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]=[C:14]=[O:15])[C:3]([CH3:8])([CH3:7])[N:4]=[C:5]=[O:6].[O:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.[CH:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[CH2:22].[N-]=[C:30]=[O:31].[CH3:32]O>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>[CH:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:5](=[O:6])[NH:4][C:3]([CH3:7])([CH3:8])[CH:2]([CH3:1])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:15])[O:16][CH2:20][CH2:19][CH2:18][CH2:17][O:31][CH:30]=[CH2:32])=[CH2:22]

参加物

7

反応物 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 873291,4-Butanediol monovinyl etherHCID 105034IsocyanateHCID 3033881Trimethylhexa-1,6-diyl diisocyanate

生成物 1

HCID 87462387Bis [4-(vinyloxy)butyl]trimethyl-1,6-hexanediylbiscarbamate収率 89%

試薬・触媒・溶媒 1

HCID 9809426Di-n-butyldilauryltin触媒

実験手順

To a 2 L three neck flask equipped with a stopper, dropping funnel, stir bar, and reflux condenser was added trimethyl-1,6-diisocyanatohexane (mixture of 2,2,4- and 2,4,4-isomers, 118.7 g, 0.57 mol, obtained from Sigma-Aldrich, Milwaukee, Wis.), dibutyltin dilaurate (3.56 g, 5.6 mmol, obtained from Sigma-Aldrich) and anhydrous tetrahydrofuran (1 L). 1,4-Butanediol vinyl ether (133.2 g, 1.2 mol, obtained from Sigma-Aldrich) was added slowly dropwise to the stirring solution via the addition funnel. The reaction mixture was brought to reflux and was kept at this temperature until deemed complete by infrared spectroscopy (about 5 hours, confirmed by the disappearance of the isocyanate peak at 2200 cm−1). When the reaction was complete, methanol (500 mL) was added to quench any residual isocyanate and the solution was stirred for 0.5 hour. The solvent was stripped in vacuo and the residual oil was triturated with hexane (3×500 mL), dissolved in methylene chloride (1 L), washed with water (1×750 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 221 g of a pale yellow oil (89 percent yield). The product was believed to be a mixture of compounds of the formulae

後処理

  1. temperaturereflux condenser
  2. temperatureto reflux
  3. customabout 5 hours
  4. customto quench any residual isocyanate
  5. stirringthe solution was stirred for 0.5 hour
  6. customthe residual oil was triturated with hexane (3×500 mL)
  7. dissolutiondissolved in methylene chloride (1 L)
  8. washwashed with water (1×750 mL)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cac7159cee7242ea830ce81a0c7fff24
出典データセット
uspto-grants-2010_04
特許番号
US07699922B2

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