Triethylamine → HCID 86654290, compound

HRID 1468629Notes

Reaction equation

HRID 1468629 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][OH:7])=[N+:2]=[N-:3].C(N(CC)CC)C.[CH2:15]([S:27][C:28]([S:30][C:31]([CH3:36])([CH3:35])[C:32](Cl)=[O:33])=[S:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(Cl)Cl>[N:1]([CH2:4][CH2:5][CH2:6][O:7][C:32](=[O:33])[C:31]([S:30][C:28]([S:27][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[S:29])([CH3:36])[CH3:35])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109969743-Azidopropan-1-olHCID 87217347HCID 87217347, compound

Product 1

HCID 86654290HCID 86654290, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

3-Azidopropanol (265 mg, 2.62 mmol, 1.0 equiv) is dissolved in methylene chloride (5 mL) in a 50 mL round-bottom flask, and the solution is cooled to approximately 0° C. A solution of triethylamine (0.73 mL) in methylene chloride (5 mL) is added dropwise over 10 min. A solution of DMP-Cl (1.0 g, 2.6 mmol) in methylene chloride (5 mL) is added dropwise, and the solution is allowed to reach room temperature while stirring for 3 h. The solution is concentrated under reduced pressure, diluted with ethyl ether (100 mL), and washed with saturated aqueous sodium bicarbonate solution (50 mL), water (50 mL), and saturated NaCl solution (50 mL), successively. The organic layer is separated, dried over MgSO4 (1.0 g), and filtered. The supernatant is concentrated under reduced pressure to yield the product (1.05 g, 90% yield) as a residual oil.

Workup

  1. customto reach room temperature
  2. concentrationThe solution is concentrated under reduced pressure
  3. additiondiluted with ethyl ether (100 mL)
  4. washwashed with saturated aqueous sodium bicarbonate solution (50 mL), water (50 mL), and saturated NaCl solution (50 mL)
  5. customThe organic layer is separated
  6. dry with materialdried over MgSO4 (1.0 g)
  7. filtrationfiltered
  8. concentrationThe supernatant is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a25a1dbc964e437798ee9032a69479a8
Source dataset
uspto-grants-2015_04
Patent number
US09006193B2

Reaction notes

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