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

HRID 247082

Reaction equation

HRID 247082 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); 1690cm-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-e11945b33d024b56ad1a7d429e375eb8
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Linked notes

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