Diethyl Ether → 2,4-Dichloro-6-methyl-1,3,5-triazine

HRID 1811772Notes

Reaction equation

HRID 1811772 reaction equation
C[Mg]Br.CCO[CH2:7][CH3:8].[Cl:9][C:10]1[N:15]=C(Cl)[N:13]=[C:12]([Cl:17])[N:11]=1.C(Cl)Cl.[O-][Mn](=O)(=O)=O.[K+]>>[Cl:9][C:10]1[N:11]=[C:12]([Cl:17])[N:13]=[C:7]([CH3:8])[N:15]=1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 7954Cyanuric chlorideHCID 516875Potassium PermanganateHCID 178418573HCID 178418573, compound

Product 1

HCID 160832,4-Dichloro-6-methyl-1,3,5-triazineYield 90%

Procedure

Methylmagnesium bromide, 3M in ether (Aldrich, St. Louis, Mo.) (10.0 mL, 30 mmol) was added slowly to a white suspension of 2,4,6-trichloro-1,3,5-triazine (Aldrich, St. Louis, Mo.) (3.68 g, 20 mmol) in DCM (25.0 mL, 389 mmol) at 0° C. and the resulting yellow suspension was warmed up to room temperature and stirring was continued until disappearance of starting material (TLC, KMnO4 stain, 3H). The reaction was carefully quenched with NH4Cl(aq) at 0° C. and then diluted with water and DCM (25.0 mL). The separated organic layer was dried, filtered and concentrated to give 2,4-dichloro-6-methyl-1,3,5-triazine as a yellow solid (2.94 g, 90%) which was used for further reaction without purification. 1H-NMR (CDCl3, 400 MHz) δ 2.74 (s, 3H).

Workup

  1. customThe reaction was carefully quenched with NH4Cl(aq) at 0° C.
  2. additiondiluted with water and DCM (25.0 mL)
  3. customThe separated organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-27da382713404f10911dfc7af3997524
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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