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

HRID 1942890Notes

Reaction equation

HRID 1942890 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[CH3:11][Zn]C.C1(C)C=CC=CC=1.O>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([O:9][CH3:10])[N:5]=[C:6]([CH3:11])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 192672,4-Dichloro-6-methoxy-3,5-triazineHCID 178477796HCID 178477796, compound

Product 1

HCID 193920792-Chloro-4-methoxy-6-methyl-1,3,5-triazineYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2,4-dichloro-6-methoxy-1,3,5-Triazine (1.0 g, 5.56 mmol) in 10 ml of dioxane was treated with a 1.2 molar solution of dimethylzinc in toluene (4.63 ml, 5.56 mmol). The mixture was stirred overnight at room temperature, poured into 100 ml of water and extracted with ethyl acetate. Chromatography on silica gel using heptane/ethyl acetate 9:1 v/v gave the title compound (225 mg, 25%) as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-fab080aaad9b447d8fcd508bddbb2ae4
Source dataset
uspto-grants-2013_03
Patent number
US08389717B2

Reaction notes

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