Water → 2-Chloro-4-methyl-6-phenyl-1,3,5-triazine

HRID 635893Notes

Reaction equation

HRID 635893 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[CH3:15][Mg]Br.O1CCCC1.O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH3:15])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 155492,4-Dichloro-6-phenyl-1,3,5-triazineHCID 178420675HCID 178420675, compound

Product 1

HCID 356892-Chloro-4-methyl-6-phenyl-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Step 2) In 85 ml of dry tetrahydrofuran was dissolved 17 g of 2,4-dichloro-6-phenyl-1,3,5-triazine. To this solution on an ice-water bath was added 135 ml of 1M methylmagnesium bromide-tetrahydrofuran dropwise over about 30 minutes. After completion of dropwise addition, the mixture was stirred at room temperature for 2 hours. This reaction mixture was poured into iced water and extracted with ethyl acetate. The extract was washed with water, dried over MgSO4, and concentrated. The residue was purified with silica gel column chromatography to provide 3.6 g of the title compound as white crystals.

Workup

  1. additionAfter completion of dropwise addition
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-d0135db25a814c05a50342020495c5f3
Source dataset
uspto-grants-2001_02
Patent number
US06191149B1

Reaction notes

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