Triethylamine → HCID 22181159, compound

HRID 1796200Notes

Reaction equation

HRID 1796200 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][N:12]([S:19]([CH3:18])(=[O:21])=[O:20])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22181052HCID 22181052, compound

Product 1

HCID 22181159HCID 22181159, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-chloro-4-(piperidin-4-yloxy)nitrobenzene (1.00 g) obtained in reference example 8 in dichloromethane (20 ml) were added successively methanesulfonyl chloride (0.33 ml) and triethylamine (1.09 ml) with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, the reaction mixture was diluted with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1) as the eluent to afford the title compound (0.96 g, yield: 73%) as a colorless amorphous solid.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 2 hours
  3. stirringAfter stirring
  4. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2e0d54aa6520414884dc40a8e5d40501
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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