Triethylamine → 1-(4-Chlorophenoxy)methyl-5-trifluoromethylpyrimidin-2-one

HRID 1982569Notes

Reaction equation

HRID 1982569 reaction equation
Cl[CH2:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[F:11][C:12]([F:21])([F:20])[C:13]1[CH:14]=[N:15][C:16](=[O:19])[NH:17][CH:18]=1.C(N(CC)CC)C>ClCCl>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:2][N:17]2[CH:18]=[C:13]([C:12]([F:20])([F:21])[F:11])[CH:14]=[N:15][C:16]2=[O:19])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 88801alpha,4-DichloroanisoleHCID 133170275-(Trifluoromethyl)pyrimidin-2(1H)-one

Product 1

HCID 133170311-(4-Chlorophenoxy)methyl-5-trifluoromethylpyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-chloromethoxy-4-chloro-benzene [see Preparation 11](0.35 mmol) in dichloromethane (1 ml) was added with stirring at room temperature to a solution prepared from 5-trifluoromethyl-pyrimidin-2-one (0.33 mmol) and triethylamine (0.33 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature for 24 h and then it was stirred at 70° C. for 30 min, the solvent was then distilled off, the residue triturated with water, the residual material extracted with chloroform and the dried (MgSO4) chloroform solution evaporated to yield the product, 60 mg (62%), as a mixture of the N- and O-isomers in the ratio 5:1. The isomers were separated by their different solubilities in ether, the O-isomer being the more soluble. The title compound, the N-isomer had m.p. 98° C. (Found C46.78; H2.88. Calc. for C12H8ClF3N2O3 : C47.30; H2.65) 1H NMR (CDCl3); δ 5.85 (CH2), 6.8-7.4 (Ph), 8.15 (H-4, J4.6 3 Hz) 8.76 (H-6) MS [70 eV; m/z (% rel. int.)]; 177 (100), 150(10), 75(5), IR (KBr); 1690 cm-1 (CO).

Workup

  1. stirringThe mixture was stirred at room temperature for 24 h
  2. stirringit was stirred at 70° C. for 30 min
  3. distillationthe solvent was then distilled off
  4. customthe residue triturated with water
  5. extractionthe residual material extracted with chloroform
  6. dry with materialthe dried (MgSO4) chloroform solution
  7. customevaporated
  8. customto yield the product, 60 mg (62%)
  9. additionas a mixture of the N-
  10. customThe isomers were separated by their different solubilities in ether

Sources & evidence

ORD record
ord-9ac24d7d4140418d98f704f9d76d6e56
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Reaction notes

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