Hydrochloric Acid → 2,4-Dichloro-6-methyl-1,3,5-triazine

HRID 2371752Notes

Reaction equation

HRID 2371752 reaction equation
[N-:1](C#N)[C:2]#[N:3].[Na+].[ClH:7].[CH3:8][NH:9][C:10](=O)[CH3:11].P(Cl)(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[Cl:7][C:8]1[N:3]=[C:2]([Cl:15])[N:1]=[C:10]([CH3:11])[N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6582N-MethylacetamideHCID 24813Phosphorus oxychlorideHCID 4350929Sodium dicyanamide

Product 1

HCID 160832,4-Dichloro-6-methyl-1,3,5-triazineYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 500 ml flask equipped with a mechanical stirrer, a reflux condenser, a thermometer and a gas inlet was placed 25 g of sodium dicyanamide and 250 ml of toluene. At 25°-35° C., 31 g of HCl gas was introduced. The white slurry was stirred for an additional 15 minutes at room temperature. Then, 21 g of N-methylacetamide and 43.5 g of phosphorus oxychloride were charged. After stirring for 5 minutes, the reaction mixture was heated to 85° C. for 1.5 hours and then to 110° C. for an hour. It was cooled to 25° C. and then poured into 500 ml of ice water. After extraction with an additional 250 ml of toluene, the combined toluene extracts were dried over MgSO4, filtered and evaporated to give 26 g of 2,4-dichloro-6-methyl-1,3,5-triazine (58% yield) as white needles.

Workup

  1. customIn a 500 ml flask equipped with a mechanical stirrer, a reflux condenser
  2. stirringAfter stirring for 5 minutes
  3. temperaturethe reaction mixture was heated to 85° C. for 1.5 hours
  4. waitto 110° C. for an hour
  5. temperatureIt was cooled to 25° C.
  6. extractionAfter extraction with an additional 250 ml of toluene
  7. dry with materialthe combined toluene extracts were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-a130fd2f76f34b64977603ed88ea25f8
Source dataset
uspto-grants-1992_03
Patent number
US05095113

Reaction notes

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