Ethanesulfonylchloride, 2-chloro- → HCID 66748565, compound

HRID 1622590Notes

Reaction equation

HRID 1622590 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)[CH3:3].[H-].[Na+].Cl[CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23].C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]3=[N:16][S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][N:12]3[CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)[CH3:1]

Participants

7

Reactant 4

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 64090335HCID 64090335, compound

Product 1

HCID 66748565HCID 66748565, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[4-(1-methylethyl)phenyl]pyridin-2-amine (700 mg) in dehydrated THF (15 mL) was added to a mixture of sodium hydride (60%, 659 mg) and 2-chloroethanesulfonyl chloride (1613 mg) in dehydrated THF (15 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight, and saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added. The resulting precipitate was collected by filtration, and washed with water and ethyl acetate to give the title compound (738 mg) as a white solid. The obtained solid was crystallized from acetonitrile and diisopropyl ether to give a white solid.

Workup

  1. temperaturecooling
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-198bb04987fd4ec0a7fa5fcc4633dfd9
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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