Triethylamine → HCID 59659907, compound

HRID 1865155Notes

Reaction equation

HRID 1865155 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH:4]([NH:13][C:14]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24]OCCOC)=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH2:31](OCCOCCO)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]CC.C(N(CC)CC)C>C(#N)C>[CH3:1][O:2][C:3](=[O:30])[CH:4]([NH:13][C:14]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:15])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 764572-[2-(Dodecyloxy)ethoxy]ethanolHCID 11582753HCID 11582753, compound

Product 1

HCID 59659907HCID 59659907, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Oligomer XXIV was prepared in an analogous manner to that described above for Oligomer XXII. Diethylene glycol monododecyl ether (2.712 g, 9.88 mmol) was dissolved in 100 mL dry acetonitrile. Triethylamine (2.06 mL, 14.8 mmol) and DSC (3.80 g, 14.8 mmol) were added. After stirring for 18 hours at room temperature under an inert atmosphere, the reaction mixture was concentrated in vacuo. The residual oil was taken up in concentrated sodium bicarbonate solution and extracted with EtOAc (2×200 mL). The combined EtOAc layers were washed with water (2×100 mL) and brine (2×100 mL). The organics were dried over Na2SO4, filtered and evaporated to dryness to give 3.58 g (87%) of XXIII.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionextracted with EtOAc (2×200 mL)
  3. washThe combined EtOAc layers were washed with water (2×100 mL) and brine (2×100 mL)
  4. dry with materialThe organics were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b0e98541c48f4bacba227e77f01a5459
Source dataset
uspto-grants-2009_12
Patent number
US07625995B2

Reaction notes

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