Aluminum(III) Chloride → 1-Methyl-2-sulfanylidene-6-(trifluoromethyl)-2,3-dihydropyrimidin-4(1H)-one

HRID 1166040Notes

Reaction equation

HRID 1166040 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4](CC2C=CC=CC=2)[C:3]1=[S:20].[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=C(C)C=1>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][C:5](=[O:12])[NH:4][C:3]1=[S:20]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 223409922,3-Dihydro-1-methyl-3-(phenylmethyl)-2-thioxo-6-(trifluoromethyl)-4(1H)-pynmidinone

Product 1

HCID 223409891-Methyl-2-sulfanylidene-6-(trifluoromethyl)-2,3-dihydropyrimidin-4(1H)-oneYield 48.6%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

2,3-Dihydro-1-methyl-3-(phenylmethyl)-2-thioxo-6-(trifluoromethyl)-4(1H)-pyrimidinone (1.0 g) was dissolved in m-xylene (15 ml) and anhydrous aluminum chloride (0.58 g) was added. The solution was refluxed for 4 hr and poured onto ice water. Extraction with ethyl acetate and evaporation of the solvent in vacuo afforded a residue which was triturated with diethyl ether to afford the title compound (0.34 g). 1H NMR, CDCl3, 3.86 (3H, m), 6.49 (1H, s), 10.62 (1H, br s).

Workup

  1. temperatureThe solution was refluxed for 4 hr
  2. additionpoured onto ice water
  3. extractionExtraction
  4. customwith ethyl acetate and evaporation of the solvent in vacuo
  5. customafforded a residue which
  6. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-46b48947f4d84ccbadc6444de8ee038e
Source dataset
uspto-grants-2003_09
Patent number
US06613718B2

Reaction notes

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