Triethylamine → HCID 69822950, compound

HRID 396271Notes

Reaction equation

HRID 396271 reaction equation
C([N:3](CC)CC)C.CS(Cl)(=O)=O.[CH2:13]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][OH:38])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([O:20][CH:21]([NH2:3])[CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][OH:38])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11164646Hexaethylene Glycol Monobenzyl Ether

Product 1

HCID 69822950HCID 69822950, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.45 mL, 10.74 mmol) and methanesulfonyl chloride (0.48 mL, 5.9 mmol) were added to a solution of hexaethyleneglycol monobenzyl ether (2.0 g, 5.37 mmol) in methylene chloride (30 mL) at 0° C. and the solution was stirred for 30 min at ice bath temperature. The reaction mixture was filtered and concentrated to an oil which was dissolved in 30% ammonium hydroxide solution (50 mL). The reaction mixture was heated at reflux for 3 days and concentrated. Residual water was removed by evaporation from toluene and the crude material was slurried with THF and filtered. The filtrate was concentrated at reduced pressure to provide the title compound as an amber oil (1.14 g, 57% yield). 1H-NMR (300 MHz, DMSO-d6) δ: 7.77 (br s, 2H), 7.40-7.10 (m, 5H), 4.48 (s, 2H), 3.61-3.48 (m, 24H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated to an oil which
  3. dissolutionwas dissolved in 30% ammonium hydroxide solution (50 mL)
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 3 days
  6. concentrationconcentrated
  7. customResidual water was removed by evaporation from toluene
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-33cb2cfc29fd45749494ec3637b86ad8
Source dataset
uspto-grants-2003_08
Patent number
US06608069B1

Reaction notes

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