Water → HCID 66747904, compound

HRID 1747874Notes

Reaction equation

HRID 1747874 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-a5899406a5034a9b9ed525ebf98a7a8c
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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