Trichloroacetyl chloride → 5-Chloro-6-methyl-4-trichloroacetoxy-2-trichloromethylpyrimidine

HRID 223136Notes

Reaction equation

HRID 223136 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[N:4][C:5]([C:9]([Cl:12])([Cl:11])[Cl:10])=[N:6][C:7]=1[CH3:8].C(N(CC)CC)C.[Cl:21][C:22]([Cl:27])([Cl:26])[C:23](Cl)=[O:24]>C(OCC)C>[Cl:1][C:2]1[C:3]([O:13][C:23](=[O:24])[C:22]([Cl:27])([Cl:26])[Cl:21])=[N:4][C:5]([C:9]([Cl:10])([Cl:11])[Cl:12])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 178432777HCID 178432777, compound

Product 1

HCID 130513975-Chloro-6-methyl-4-trichloroacetoxy-2-trichloromethylpyrimidineYield 35%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5.8 g (0.02 mole) 5-chloro-4-hydroxy-6-methyl-2-trichloromethylpyrimidine and 2.0 g (0.02 mole) triethylamine in 100 ml diethyl ether was added 3.6 g (0.02 mole) trichloroacetyl chloride. After the exothermic reaction subsided, the reaction mixture was stirred an additional 10 minutes and filtered. The filtrate was concentrated in-vacuo and the residue recrystallized from ligroin to give 1.6 g starting material and 2.3 g product; m.p. 92° C. The corrected yield was 35%.

Workup

  1. customAfter the exothermic reaction
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in-vacuo
  4. customthe residue recrystallized from ligroin
  5. customto give 1.6 g

Sources & evidence

ORD record
ord-3b98e946260b4a4187cdea8d9dcee02e
Source dataset
uspto-grants-1982_10
Patent number
US04352806

Reaction notes

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