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

HRID 521793Notes

Reaction equation

HRID 521793 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-Dichloropyridine (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-3ce52ca8e44a4d1a9447d3323cd95577
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

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