Water → (6-Chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine

HRID 216240

Reaction equation

HRID 216240 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[CH2:19][CH2:20][NH2:21].C(=O)(O)[O-].[Na+].O>CCO>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:21][CH2:20][CH2:19][C:13]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=2[Cl:11])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 1429382,4-DichlorophenethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 80545555(6-Chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amineYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4,6-dichloro-2-methylsulfanyl-pyrimidine (2.66 g, 13.6 mmol), 2-(2,4-dichloro-phenyl)-ethylamine (2.26 mL, 15 mmol) and sodium bicarbonate (2.29 g, 27.2 mmol) in EtOH (35 mL) is heated to 85° C. for 1 hour and poured into water (100 mL). The solid precipitate is collected by filtration and dissolved in hot EtOH (75 mL). After cooling overnight the crystals that formed are collected by filtration and dried to afford (6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine (3.43 g, 72%) as a solid.

Workup

  1. filtrationThe solid precipitate is collected by filtration
  2. dissolutiondissolved in hot EtOH (75 mL)
  3. temperatureAfter cooling overnight the crystals
  4. customthat formed
  5. filtrationare collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-b0de618506524590bcdeb5c36842485b
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Linked notes

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