p-Toluenesulfonic acid → HCID 9866840, compound

HRID 2415110Notes

Reaction equation

HRID 2415110 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:24]([CH3:27])([CH3:26])O)[CH:5]=[C:6]([O:22][CH3:23])[C:7]=1[O:8][C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:12]=[C:11]([CH3:21])[N:10]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:24]([CH3:27])=[CH2:26])[CH:5]=[C:6]([O:22][CH3:23])[C:7]=1[O:8][C:9]1[N:10]=[C:11]([CH3:21])[N:12]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:14]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15547786HCID 15547786, compound

Product 1

HCID 9866840HCID 9866840, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-bromo-4-[[6-methyl-4-(4-morpholinyl)-1,3,5-triazin-2-yl]oxy]-5-methoxy-a,a-dimethylbenzenemethanol (1.92 g) in 80 mL of benzene, a small amount of p-toluene sulfonic acid was added. The solution was refluxed under azeotropic conditions for 16 hours. Once cooled to room temperature, the solution was washed with saturated NaHCO3 followed by water. The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified on silica gel using a mixture of 1:1 ethyl acetate and hexane to yield 2-[2-bromo-6-methoxy-4-(1-methylethenyl)phenoxy]-4-methyl-6-(4-morpholinyl)-1,3,5-triazine as a colorless compound, mp 63-67° C.

Workup

  1. temperatureThe solution was refluxed under azeotropic conditions for 16 hours
  2. washthe solution was washed with saturated NaHCO3
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified on silica gel using
  6. additiona mixture of 1:1 ethyl acetate and hexane

Sources & evidence

ORD record
ord-1d745dda549a4bf69d39dd09f0ecbc34
Source dataset
uspto-grants-2004_11
Patent number
US06818648B2

Reaction notes

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