Cyanuric chloride → HCID 58799092, compound

HRID 2057062Notes

Reaction equation

HRID 2057062 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][C:17]=1[CH3:18])[NH2:14].[OH-].[Na+]>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][C:17]([CH3:18])=[C:11]([F:10])[CH:12]=2)[N:7]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 99573-Fluoro-4-methylanilineHCID 14798Sodium Hydroxide2×

Product 1

HCID 58799092HCID 58799092, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To cyanuric chloride (1.4821 g, 8 mmol) dissolved in acetone (115 mL) stiffing at 0-5° C., was added a solution of 3-fluoro-4-methylaniline (1.0017 g, 8 mmol) in acetone (15 mL) followed by the addition of 2.5 N NaOH (3.2 mL, 8 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% NaOH. The solid that formed was collected by vacuum filtration and the resulting solid was dried overnight under vacuum. The product was used with no further purification, (156a, 1.88 g, 86%), mp 130° C.; HPLC: Inertsil ODS-3V C 18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 36.8 min, 99.1% purity;

Workup

  1. customstiffing at 0-5° C.
  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
  7. customThe product was used with no further purification, (156a, 1.88 g, 86%), mp 130° C.

Sources & evidence

ORD record
ord-d7260153a3f84273a46a389042ebf4c6
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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