Cyanuric chloride → HCID 11562413, compound

HRID 2057071Notes

Reaction equation

HRID 2057071 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[F:10][C:11]1[CH:12]=[C:13]([OH:19])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].[OH-:20].[Na+].OP([O-])(O)=O.[K+]>CC(C)=O.O.CC#N.CO>[F:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[O:19][C:2]1[N:4]=[C:5]([O:20][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:11]([F:10])[CH:12]=2)[N:7]=[C:8]([O:19][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:11]([F:10])[CH:12]=2)[N:1]=1

Participants

9

Reactant 4

HCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 516951Monobasic potassium phosphateHCID 146616133-Fluoro-4-methoxyphenol

Product 1

HCID 11562413HCID 11562413, compoundYield 15%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
2.5 °C

Procedure

Cyanuric chloride (0.9207 g, 5 mmol) was dissolved in acetone (20 mL). The solution was cooled to 0-5° C. with an ice bath. To the cooled solution mixture of 3-fluoro-4-methoxy-phenol (0.7142 g, 5 mmol) in acetone (20 mL), was added dropwise 2.5 N NaOH (20 mL, 50 mmol) and water (5 mL). The reaction mixture was allowed to stir at 0-5° C. for 1 hour under nitrogen. The reaction mixture was diluted with cold water (20 mL) and the resulting solid was collected by vacuum filtration. The white solid was dried overnight under vacuum to give 303 mg of E64 (15% yield), mp>210° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 3.5 min, 99.7% purity; MS (TOF MS ES+): m/z 502 (M+H, 100), 406 (61.3), 392 (44.1).

Workup

  1. filtrationthe resulting solid was collected by vacuum filtration
  2. customThe white solid was dried overnight under vacuum
  3. customto give 303 mg of E64 (15% yield), mp>210° C.

Sources & evidence

ORD record
ord-4ac0fd3e03964672a9cde8a554a40c77
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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