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

HRID 2266955Notes

Reaction equation

HRID 2266955 reaction equation
C[Mg]Br.CCO[CH2:7][CH3:8].[N:9]1[C:16]([Cl:17])=[N:15]C(Cl)=[N:12][C:10]=1[Cl:11]>ClCCl.O>[Cl:11][C:10]1[N:9]=[C:16]([Cl:17])[N:15]=[C:7]([CH3:8])[N:12]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 7954Cyanuric chlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 160832,4-Dichloro-6-methyl-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of methylmagnesium bromide in ether (3M, 30 ml, 90 mmole) was added dropwise to a stirred solution of cyanuric chloride (3.91 g, 21.20 mmole) in anhydrous dichloromethane at −10° C. After the addition was complete, the reaction mixture was stirred at −5° C. for 4 h, after which time water was added dropwise at a rate such that the temperature of the reaction stayed below 10° C. After warming to room temperature, the reaction mixture was diluted with additional water and methylene chloride and passed through a pad of cilite. The organic layer was dried and evaporated to give 2,4-dichloro-6-methyl-1,3,5-triazine of 4 as yellow solids (3.02 g, 87%). 1H NMR (CDCl3) δ 2.70 (s, 3H).

Workup

  1. additionAfter the addition
  2. customstayed below 10° C
  3. temperatureAfter warming to room temperature
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-0260c885c2584b27a8316222fb9d699a
Source dataset
uspto-grants-2010_12
Patent number
US07858782B2

Reaction notes

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