Water → HCID 66747989, compound

HRID 1747889Notes

Reaction equation

HRID 1747889 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[C:20]1[C:21]([NH2:26])=[N:22][CH:23]=[CH:24][CH:25]=1.O>C1COCC1.CCCCCC>[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[C:20]1[C:21]2=[N:26][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:22]2[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 64089232HCID 64089232, compound

Product 1

HCID 66747989HCID 66747989, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a suspension of 60% sodium hydride (0.79 g) in THF (20 mL) was added 2-chloroethanesulfonyl chloride (1.93 g) under ice-cooling. The reaction mixture was stirred under ice-cooling for 5 min. Then, a solution of 3-(naphthalen-2-yl)pyridin-2-amine (0.87 g) in THF (20 mL) was added. The reaction mixture was stirred at room temperature overnight and at 50° C. for 1 hr, and water and hexane were added under ice-cooling. The resulting solid was collected by filtration, washed with diisopropyl ether, and dried under reduced pressure to give the title compound (0.88 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 5 min
  3. stirringThe reaction mixture was stirred at room temperature overnight and at 50° C. for 1 hr
  4. temperaturecooling
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with diisopropyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-a084c743e9c84158b8f7f9e4fe104aa6
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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