2-Chloro-4,6-dimethoxy-1,3,5-triazine → 7-[(4,6-dimethoxy-1,3,5-triazin-2-yl)oxy]-3-methyl-isobenzofuran-1(3H)-thione

HRID 22170

Reaction equation

HRID 22170 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[S:11])[O:8][CH:7]2[CH3:12].[H-].[Na+].[H][H].Cl[C:18]1[N:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([O:26][CH3:27])[N:19]=1>CN(C)C=O>[CH3:27][O:26][C:20]1[N:21]=[C:22]([O:24][CH3:25])[N:23]=[C:18]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:10]=2[C:9](=[S:11])[O:8][CH:7]3[CH3:12])[N:19]=1

Participants

6

Reactant 4

HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 24758Sodium hydrideHCID 1355484557-hydroxy-3-methylisobenzofuran-1(3H)-thioneHCID 178418361HCID 178418361, compound

Product 1

HCID 199274287-[(4,6-dimethoxy-1,3,5-triazin-2-yl)oxy]-3-methyl-isobenzofuran-1(3H)-thione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g of 7-hydroxy-3-methyl-isobenzofuran-1(3H)-thione is introduced into a suspension of 0.15 g of sodium hydride in absolute dimethylformamide and, when the evolution of hydrogen has ceased, 1.0 g of 2-chloro-4,6-dimethoxy-1,3,5-triazine is added thereto. The reaction mixture is subsequently stirred at room temperature for 5 hours, ice-water is then added and the whole is extracted with ethyl acetate and washed with sodium chloride solution. The crude product, having been concentrated by evaporation, is purified by chromatography (eluant: 45% ethyl acetate in n-hexane) and recrystallised from acetone/n-hexane to yield 7-[(4,6-dimethoxy-1,3,5-triazin-2-yl)oxy]-3-methyl-isobenzofuran-1(3H)-thione in the form of yellow crysals, m.p. 177°-178° C.; IR spectrum (CHCl3): 1590, 1560, 1366, 1304, 1140 cm-1 ; 1H-NMR (CDCl3): 5.81 ppm (q, 1H), 1.73 ppm (d, 3H).

Workup

  1. extractionthe whole is extracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. concentrationThe crude product, having been concentrated by evaporation
  4. customis purified by chromatography (eluant: 45% ethyl acetate in n-hexane)
  5. customrecrystallised from acetone/n-hexane

Sources & evidence

ORD record
ord-6bb2c1b7ef404f27a231b4a9a16bd962
Source dataset
uspto-grants-1995_06
Patent number
US05428002

Linked notes

Loading…