Methyl trifluoroacetate → 4-Methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-amine

HRID 1598945Notes

Reaction equation

HRID 1598945 reaction equation
[C:1]([NH:3][C:4]([NH2:6])=[NH:5])#[N:2].[F:7][C:8]([F:14])([F:13])[C:9](OC)=O.[CH3:15][O-:16].[Na+]>[Cl-].[Zn+2].[Cl-].CO>[NH2:5][C:4]1[N:6]=[C:9]([C:8]([F:14])([F:13])[F:7])[N:2]=[C:1]([O:16][CH3:15])[N:3]=1

Participants

6

Reactant 3

HCID 9893Methyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 178418324HCID 178418324, compound

Product 1

HCID 1999484-Methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-amineYield 89%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

21 g (0.25 mol) of N-cyanoguanidine, 3.4 g (0.025 mol) of anhydrous zinc chloride and 160 g (1.25 mol) of methyl trifluoroacetate are initially introduced into 400 ml of methanol, the mixture is warmed to 50° C. and 50 g (0.27 mol) of 30% strength sodium methoxide solution are pumped in in the course of 10 hours. The solvent is then largely removed, and the residue is washed with 250 ml of water and 250 ml of dilute hydrochloric acid and dried at 60° C./20 mbar. 43.2 g (0.22 mol, 89%) of 2-amino-4-trifluoromethyl-6-methoxy-1,3,5-triazine are obtained in the form of a colorless powder (HPLC: >99% by weight) M.p.: 161°-163.5° C.

Workup

  1. customare pumped in in the course of 10 hours
  2. customThe solvent is then largely removed
  3. washthe residue is washed with 250 ml of water and 250 ml of dilute hydrochloric acid
  4. customdried at 60° C./20 mbar

Sources & evidence

ORD record
ord-dcaf4672fd02481fbfdf148f3c173295
Source dataset
uspto-grants-1998_04
Patent number
US05739328

Reaction notes

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