Chlorine → 4-Chloro-6-(2-Fluoropropan-2-Yl)-1,3,5-Triazin-2-Amine

HRID 891217Notes

Reaction equation

HRID 891217 reaction equation
[Cl:1]Cl.[NH2:3][C:4]1[N:9]=[C:8](SC)[N:7]=[C:6]([C:12]([F:15])([CH3:14])[CH3:13])[N:5]=1>C(O)(=O)C>[NH2:3][C:4]1[N:9]=[C:8]([Cl:1])[N:7]=[C:6]([C:12]([F:15])([CH3:14])[CH3:13])[N:5]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 112757034-(1-Fluoro-1-methylethyl)-6-(methylthio)-1,3,5-triazin-2-amine

Product 1

HCID 114468284-Chloro-6-(2-Fluoropropan-2-Yl)-1,3,5-Triazin-2-AmineYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

Chlorine gas was passed at 20 to 25° C. into a suspension of 150 g of 2-amino-4-methylthio-6-(1-fluoroisopropyl)-1,3,5-triazine in 1 liter of glacial acetic acid (15 min). The reaction mixture was stirred for 30 min at approx. 20° C., flushed with nitrogen gas for 1 h at room temperature, poured into 5 liters of ice-cold aqueous solution of 350 g of sodium hydroxide and stirred for 5 min. After filtration with suction and drying, 110 g (80%) of 2-amino-4-chloro-6-(1-fluoroisopropyl)-1,3,5-triazine were obtained as a white powder (m.p. 185° C.).

Workup

  1. customflushed with nitrogen gas for 1 h at room temperature
  2. additionpoured into 5 liters of ice-cold aqueous solution of 350 g of sodium hydroxide
  3. stirringstirred for 5 min
  4. filtrationAfter filtration with suction
  5. customdrying

Sources & evidence

ORD record
ord-901473c1e11549a0abac5470f10abff1
Source dataset
uspto-grants-2006_02
Patent number
US07002011B1

Reaction notes

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