Water → HCID 66747904, compound

HRID 2035760Notes

Reaction equation

HRID 2035760 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][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.[H-].[Na+].Cl[CH2:22][CH2:23][S:24](Cl)(=[O:26])=[O:25].O>C1COCC1.CCCCCC>[F:18][C:2]([F:1])([F:17])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]3=[N:16][S:24](=[O:26])(=[O:25])[CH2:23][CH2:22][N:12]3[CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 65551364HCID 65551364, compound

Product 1

HCID 66747904HCID 66747904, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A mixture of 3-[4-(trifluoromethoxy)phenyl]pyridin-2-amine (350 mg) in dehydrated THF (5 mL) was added to a mixture of sodium hydride (60%, 275 mg) and 2-chloroethanesulfonyl chloride (673 mg) in dehydrated THF (5 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight, and water and hexane were added. The resulting precipitate was collected by filtration, and washed with water and diisopropyl ether to give the title compound (333 mg) as a white solid. The obtained solid was crystallized from THF, 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 diisopropyl ether

Sources & evidence

ORD record
ord-4638e59fc3c94ea4b2ff2fc74537cc67
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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