Cyanuric chloride → HCID 21897019, compound

HRID 916115Notes

Reaction equation

HRID 916115 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×

Conditions

Temperature
2.5 °C

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. extractionThe reaction mixture was extracted three times
  2. washthe combined organic layer were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe sample was concentrated in vacuo
  5. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-227b9983506f4dc0bc7d06295e6487e9
Source dataset
uspto-grants-2007_09
Patent number
US07268134B2

Reaction notes

Loading…