Methanethiol → Ametryn

HRID 370611

Reaction equation

HRID 370611 reaction equation
[Na].[CH3:2][SH:3].[CH3:4][CH2:5][NH:6][C:7]1[N:12]=[C:11](Cl)[N:10]=[C:9]([NH:14][CH:15]([CH3:17])[CH3:16])[N:8]=1>CO>[CH3:2][S:3][C:11]1[N:10]=[C:9]([NH:14][CH:15]([CH3:17])[CH3:16])[N:8]=[C:7]([NH:6][CH2:5][CH3:4])[N:12]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 2256AtrazineHCID 5360545Sodium

Product 1

HCID 13263Ametryn

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of sodium was added to 100 ml of dry methanol. The solution was allowed to cool to room temperature, 12 g of methanethiol was added, then 4.5 g atrazine, and the mixture was refluxed for 2 hours. The solvent was evaporated, the residue was dissolved in water, and the solution was extracted with ether. The extract phase was dried (MgSO4) and the solvent was evaporated. The residue was dissolved in a minimum amount of boiling hexane. The solution was cooled and the solid product was collected and dried to give 2-(methylthio)-4-(1-methylethylamino)-6-(ethylamino)-1,3,5-triazine (15A) (Ametryne).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. extractionthe solution was extracted with ether
  4. dry with materialThe extract phase was dried (MgSO4)
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in a minimum amount of boiling hexane
  7. temperatureThe solution was cooled
  8. customthe solid product was collected
  9. customdried

Sources & evidence

ORD record
ord-cbe7ab5bfd714a279eaa03515efbabb1
Source dataset
uspto-grants-1985_07
Patent number
US04528027

Linked notes

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