Hydrochloric Acid → 4,6-dichloro-N-(3-fluorophenyl)-1,3,5-triazin-2-amine

HRID 2057066Notes

Reaction equation

HRID 2057066 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].[OH-].[Na+].Cl>CC(C)=O>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:11]([F:10])[CH:12]=2)[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7954Cyanuric chlorideHCID 97423-FluoroanilineHCID 14798Sodium Hydroxide2×

Product 1

HCID 10747054,6-dichloro-N-(3-fluorophenyl)-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To cyanuric chloride (1.6614 g, 9 mmol) dissolved in acetone (20 mL) stirring at 0-5° C., was added a solution of 3-fluoroaniline (0.9 mL, 9 mmol) in acetone (5 mL) followed by the addition of 2.5 N NaOH (3.6 mL, 9 mmol). The reaction mixture was allowed to stir at 0-5° C. for 1 hour under nitrogen. The reaction mixture was poured over crushed ice and neutralized with 10% HCl and 10% NaOH. The solid that formed was collected by vacuum filtration and the resulting solid was dried overnight under vacuum. Flash column chromatography (SiO2, 70:30 hexanes:ethyl acetate) yielded a faint yellow solid (159a, 1.67 g, 72%), mp 143° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 23.5 min, 87.0% purity.

Workup

  1. stirringto stir at 0-5° C. for 1 hour under nitrogen
  2. additionThe reaction mixture was poured
  3. customover crushed ice
  4. customThe solid that formed
  5. filtrationwas collected by vacuum filtration
  6. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-b9cc64c260e34fcf97f523fda7d482bd
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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