Water → 4-(2-Chloro-pyridin-4-ylsulfanyl)-phenylamine

HRID 1402510Notes

Reaction equation

HRID 1402510 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([S:22][C:19]2[CH:20]=[CH:21][C:16]([NH2:15])=[CH:17][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145104-AminothiophenolHCID 335152,4-Dichloropyridine

Product 1

HCID 581678724-(2-Chloro-pyridin-4-ylsulfanyl)-phenylamineYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-Dichloropyrdine (4.44 g, 30.0 mmol) and potassium carbonate (8.28 g, 60.0 mmol) in dimethylformamide (60 mL) was purged with nitrogen for 10 min. 4-Aminothiophenol (3.76 g, 30.0 mmol) was added and the mixture stirred under nitrogen at room temperature for 18 h. Water (300 mL) was added and the slurry stirred for 30 min. The resulting solid was filtered, washed with water and vacuum dried at room temperature. Recrystallization from ethyl acetate (35 mL), filtered hot, then cooled gave 4-(2-Chloro-pyridin-4-ylsulfanyl)-phenylamine (3.946 g, 56% yield).

Workup

  1. stirringthe slurry stirred for 30 min
  2. filtrationThe resulting solid was filtered
  3. washwashed with water and vacuum
  4. customdried at room temperature
  5. customRecrystallization from ethyl acetate (35 mL)
  6. filtrationfiltered hot
  7. temperaturecooled

Sources & evidence

ORD record
ord-71324152070a432297dea6babf93155f
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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