Cyanuric chloride → HCID 21897019, compound

HRID 1375458Notes

Reaction equation

HRID 1375458 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([Cl:18])[CH:12]=1>CC(C)=O>[Cl:18][C:13]1[CH:12]=[C:11]([NH:10][C:2]2[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([Cl:6])[N:4]=2)[CH:16]=[CH:15][C:14]=1[OH:17]

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 775784-Amino-2-chlorophenol

Product 1

HCID 21897019HCID 21897019, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Cyanuric chloride (12.95 g, 70.0 mmol) was dissolved in acetone (200 mL), the solution was cooled to 0–5° C. with an ice bath, and 4-amino-2-chlorophenol (10.09 g, 70.0 mmol) in acetone (100 mL) was added. The mixture was stirred at 0–5° C. for 1 hour under nitrogen. The reaction mixture was extracted three times using dichloromethane; the combined organic layer were washed with brine and dried over sodium sulfate. The sample was concentrated in vacuo, and the resulting solid was dried overnight under vacuum to yield E6 (20.2 g, 99%); mp 180° C.; HPLC: Inertsil ODS 3V C18, 40:30:30 v:v:v [KH2PO4 (0.01 M, pH 3.2): CH3OH:CH3CN], 264 nm, Rt 11.6 min, 99.4% purity; MS (TOF ES+) m/z 293 (97.5), 291 (M+H, 100).

Workup

  1. temperaturethe solution was cooled to 0–5° C. with an ice bath
  2. extractionThe reaction mixture was extracted three times
  3. washthe combined organic layer were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe sample was concentrated in vacuo
  6. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-d9747497a3ad4b8283abe137065436eb
Source dataset
uspto-grants-2007_01
Patent number
US07169784B2

Reaction notes

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