Mesitylene → HCID 21200188, compound

HRID 1066446Notes

Reaction equation

HRID 1066446 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:26]1([CH3:34])[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=1>>[O:15]([C:4]1[N:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:7]=[C:2]([C:27]2[C:28]([CH3:33])=[CH:29][C:30]([CH3:32])=[CH:31][C:26]=2[CH3:34])[N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 7947MesityleneHCID 180882-chloro-4,6-diphenoxy-1,3,5-triazineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21200188HCID 21200188, compound

Procedure

A 250-mL reaction flask fitted with a magnetic stirrer and a condenser is charged with 21.0 g (0.070 mol) of the product of Example 15, 100 mL of mesitylene and 9.30 g (0.070 mol) of aluminum chloride. The mixture is refluxed for three days. The mixture is then poured onto ice and the phases are separated. The organic phase is dried over anhydrous sodium sulfate and the solvent is removed under reduced pressure to give a brown resin. The crude resin is recrystallized from ligroin to give 7.9 g of the title compound as a white powder melting at 135-143° C.

Workup

  1. customA 250-mL reaction flask
  2. customfitted with a magnetic stirrer and a condenser
  3. temperatureThe mixture is refluxed for three days
  4. additionThe mixture is then poured onto ice
  5. customthe phases are separated
  6. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  7. customthe solvent is removed under reduced pressure
  8. customto give a brown resin
  9. customThe crude resin is recrystallized from ligroin

Sources & evidence

ORD record
ord-c849eb90731d4e858f26d965c92cb09b
Source dataset
uspto-grants-2001_06
Patent number
US06242598B1

Reaction notes

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