2,3-Dimethylaniline → 6-Chloro-N-(2,3-dimethylphenyl)-2-(octylsulfanyl)pyrimidin-4-amine

HRID 637938Notes

Reaction equation

HRID 637938 reaction equation
[CH2:1]([S:9][C:10]1[N:15]=[C:14](Cl)[CH:13]=[C:12]([Cl:17])[N:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([O-])([O-])=O.[Na+].[Na+].[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=1[CH3:32]>C(O)C>[CH2:1]([S:9][C:10]1[N:11]=[C:12]([Cl:17])[CH:13]=[C:14]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=2[CH3:32])[N:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 68932,3-DimethylanilineHCID 10340Sodium CarbonateHCID 134137254,6-Dichloro-2-(octylsulfanyl)pyrimidine

Product 1

HCID 134137406-Chloro-N-(2,3-dimethylphenyl)-2-(octylsulfanyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-octylthio-4,6-dichloropyrimidine (3 g) in ethanol (25 ml), 2,3-xylidine (1,5 ml) and anhydrous Na2CO3 (1.25 g) are added; the mixture is refluxed for 20 hours. The residue is hot filtered and the solvent is evaporated. The residue is purified by chromathography on silica gel, yielding 1.9 g of 2-octylthio-4-chloro-6-(2,3-xylidino)-pyrimidine (III, 35).

Workup

  1. temperaturethe mixture is refluxed for 20 hours
  2. filtrationThe residue is hot filtered
  3. customthe solvent is evaporated
  4. customThe residue is purified by chromathography on silica gel

Sources & evidence

ORD record
ord-f914c1fe74144309b8969f58fca44d9d
Source dataset
uspto-grants-1985_12
Patent number
US04559345

Reaction notes

Loading…