Sodium Hydroxide → HCID 12040787, compound

HRID 891218Notes

Reaction equation

HRID 891218 reaction equation
[Cl:1]Cl.[NH2:3][C:4]1[N:9]=[C:8](SC)[N:7]=[C:6]([CH:12]([F:14])[CH3:13])[N:5]=1.[OH-].[Na+]>C(O)(=O)C>[NH2:3][C:4]1[N:9]=[C:8]([Cl:1])[N:7]=[C:6]([CH:12]([F:14])[CH3:13])[N:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24526ChlorineHCID 222449654-(1-Fluoroethyl)-6-(methylthio)-1,3,5-triazin-2-amine

Product 1

HCID 12040787HCID 12040787, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

Chlorine gas was passed into a suspension of 38 g of 2-amino-4-methylthio-6-(1-fluoroethyl)-1,3,5-triazine in 0.25 l of glacial acetic acid (15 min) at 20 to 25° C. The reaction mixture was stirred for 30 min at approx. 20° C., sprayed for 1 hour with nitrogen gas at room temperature, poured into 1.25 l of ice-cold aqueous solution of 87 g of sodium hydroxide and stirred for 5 min. After extraction with ethyl acetate, the organic phase was washed with water and dried over magnesium sulfate, and the solvent was removed in vacuo. The crude product was purified by stirring in heptane. After filtration with suction and drying, 25 g (70%) of 2-amino-4-chloro-6-(1-fluoroethyl)-1,3,5-triazine were obtained as a white powder (m.p. 131° C.); 1H NMR (CDCl3): δ=1.7 (dd, 3 H), 5.4 (dq, 1 H), 6.1 (s br., 1 H), 6.7 (s br., 1H).

Workup

  1. waitsprayed for 1 hour with nitrogen gas at room temperature
  2. stirringstirred for 5 min
  3. extractionAfter extraction with ethyl acetate
  4. washthe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe crude product was purified
  8. stirringby stirring in heptane
  9. filtrationAfter filtration with suction
  10. customdrying

Sources & evidence

ORD record
ord-723b383e40c342508da3f2f11da2cb75
Source dataset
uspto-grants-2006_02
Patent number
US07002011B1

Reaction notes

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