Water → 9-(4-Cyclohexylphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1405665Notes

Reaction equation

HRID 1405665 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26].O>C1COCC1>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:14]4=[N:19][S:25](=[O:27])(=[O:26])[CH2:24][CH2:23][N:15]4[CH:16]=[CH:17][CH:18]=3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 655495323-(4-Cyclohexylphenyl)pyridin-2-amine

Product 1

HCID 668237219-(4-Cyclohexylphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-(4-cyclohexylphenyl)pyridin-2-amine (57 mg) in dehydrated THF (5 mL) was added to a mixture of sodium hydride (60%, 45.2 mg) and 2-chloroethanesulfonyl chloride (110 mg) in dehydrated THF (5 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight, and water was added. The resulting precipitate was collected by filtration, and washed with water and diisopropyl ether to give the title compound (40.3 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 diisopropyl ether

Sources & evidence

ORD record
ord-a6f3c5aa557146ce9dfbd4d20df4ffd5
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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