Triethylamine → HCID 86616536, compound

HRID 884150Notes

Reaction equation

HRID 884150 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[N:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[N:14]=[CH:13][C:12]([CH2:15][O:16][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68523779HCID 68523779, compound

Product 1

HCID 86616536HCID 86616536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[6-(4-nitrophenoxy)pyridin-3-yl]methanol (6.1 g, 24.8 mmol) was dissolved in dichloromethane (150 mL), and to the resulting solution was added triethylamine (4.15 mL, 29.8 mmol) under ice cooling. To the resulting solution was added dropwise methanesulfonic acid chloride (2.11 mL, 27.3 mmol), and then stirred under a nitrogen atmosphere for 30 minutes at 0° C. The reaction solution was washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. To the residue was added a mixed solvent (50 mL) of n-hexane ethyl acetate=1:1. The precipitated crystals were removed by suction filtration, to thereby yield 7.9 g of the title compound.

Workup

  1. washThe reaction solution was washed with a saturated sodium bicarbonate solution and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. additionTo the residue was added a mixed solvent (50 mL) of n-hexane ethyl acetate=1:1
  5. customThe precipitated crystals were removed by suction filtration

Sources & evidence

ORD record
ord-8ad81fe708ea44ac95d78533b2cc9e76
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

Loading…