4-Aminothiophenol → HCID 86645566, compound

HRID 577395Notes

Reaction equation

HRID 577395 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([CH3:19])=[CH:14][N:13]=1>O.CO>[Cl:11][C:12]1[N:17]=[C:16]([S:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=2)[C:15]([CH3:19])=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 145104-AminothiophenolHCID 14798Sodium HydroxideHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-

Product 1

HCID 86645566HCID 86645566, compoundYield 1,124.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium hydroxide (2.38 g, 5.9 mmol) was dissolved in water (10 mL), 4-aminothiophenol (6.77 g, 5 4 mmol) was added as a solution in methanol (25 mL) and the reaction was stirred at room temperature for 30 minutes. 2,4-Dichloro-5-methylpyrimidine (7.05 g, 4 3 mmol) was slowly added as a solution in methanol (25 mL) and the reaction was stirred at room temperature for a further 1 hour during which time a precipitate formed. This precipitate was isolated by filtration, washed with minimum ice cold diethyl ether and dried under vacuum to give 4-[(2-chloro-5-methylpyrimidin-4-yl)thio]aniline (8.49 g, 92%).

Workup

  1. stirringthe reaction was stirred at room temperature for a further 1 hour during which time a precipitate
  2. customformed
  3. customThis precipitate was isolated by filtration
  4. washwashed with minimum ice cold diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-83bfbefc551442b78d4b01a34378ac1f
Source dataset
uspto-grants-2015_05
Patent number
US09040549B2

Reaction notes

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