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

HRID 1621360Notes

Reaction equation

HRID 1621360 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, 3 h). 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-9ebab616ca9f492f8a2650554ac02b57
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…