Water → HCID 57861965, compound

HRID 1095426Notes

Reaction equation

HRID 1095426 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][OH:17])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][S:26](Cl)(=[O:28])=[O:27])[CH2:20][CH2:19]1.O>ClCCl>[O:18]1[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][S:26]([O:17][CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][N:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[N:10]=2)(=[O:27])=[O:28])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 15453277HCID 15453277, compoundHCID 57861967HCID 57861967, compound

Product 1

HCID 57861965HCID 57861965, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yloxy)ethanol (154 mg, 0.53 mmol) and tryethylamine (0.22 ml, 1.58 mmol) in dichlorometane (9 ml) was added a solution of 2-morpholinoethanesulfonyl chloride (prepared from 0.69 mmol of 2-morpholinoethanesulfonic acid and 1.14 ml of oxalyl dichloride in dichlorometane at 0° C.) and the final mixture was stirred at room temperature overnight. Water was added, the organic phase separated and the aqueous phase extracted with more dichlorometane. The combined organic phases were washed with saturated aqueous solution of NaHCO3 and water, and after drying over sodium sulphate, filtered and evaporated to dryness yielding 222 mg of crude compound. After column chromatography purification (silica gel, eluent: petroleum ether/ethyl acetate 8:2), 94 mg of 2-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yloxy)ethyl 2-morpholinoethanesulfonate as a solid was obtained, with a m.p.=120-122° C. after crystallization in acetone-petroleum ether.

Workup

  1. customthe organic phase separated
  2. extractionthe aqueous phase extracted with more dichlorometane
  3. washThe combined organic phases were washed with saturated aqueous solution of NaHCO3 and water
  4. dry with materialafter drying over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customyielding 222 mg of crude compound
  8. customAfter column chromatography purification (silica gel, eluent: petroleum ether/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-e204b5c700fe4ff7bca730d78e87f9e0
Source dataset
uspto-grants-2012_03
Patent number
US08138186B2

Reaction notes

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