Ethyl Acetate → N-(4-Chlorophenyl)-2-[2-(4-pyridyl)ethylthio]pyridine-3-carboxamide

HRID 1896681Notes

Reaction equation

HRID 1896681 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][SH:11])=[CH:5][CH:4]=1.Cl[C:13]1[C:18]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1.C(OCC)(=O)C>CN(C)C=O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:19]([C:18]2[C:13]([S:11][CH2:10][CH2:9][C:6]3[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=3)=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:20])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1509694-PyridoethanethiolHCID 5879062-chloro-N-(4-chlorophenyl)pyridine-3-carboxamide

Product 1

HCID 52948564N-(4-Chlorophenyl)-2-[2-(4-pyridyl)ethylthio]pyridine-3-carboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 60% sodium hydride (35 mg, 0.88 mmol) in N,N-dimethylformamide (1 mL), a solution of 4-pyridineethanethiol (104 mg, 0.75 mmol) in N,N-dimethylformamide (1.5 mL) and a solution of 2-chloro-N-(4-chlorophenyl)pyridine-3-carboxamide (200 mg, 0.75 mmol, Reference compound No. 2-1) in N,N-dimethylformamide (1.5 mL) were added under ice-cooling successively. The reaction mixture was stirred at room temperature for 2 hours, and then ethyl acetate (40 mL) was added thereto. The ethyl acetate layer was washed with water (40 mL) and brine (40 mL) and dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure. The precipitated solid was filtered off and washed with diethyl ether:ethyl acetate (3:1). The solid was dried under reduced pressure to give 240 mg of the target compound as a white solid. (Yield 88%)

Workup

  1. temperaturecooling successively
  2. washThe ethyl acetate layer was washed with water (40 mL) and brine (40 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. filtrationThe precipitated solid was filtered off
  6. washwashed with diethyl ether:ethyl acetate (3:1)
  7. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-06d4bc38b4774d249017c38d9cc85aaf
Source dataset
uspto-grants-2013_08
Patent number
US08518973B2

Reaction notes

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