1,2-Dichloroethane → HCID 22119889, compound

HRID 1274627Notes

Reaction equation

HRID 1274627 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]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH3:21])[C:17]=3[CH:22]=2)[C:3]1=[O:23].S(Cl)([Cl:27])(=O)=O.ClCCCl>C(Cl)Cl>[Cl:27][C:6]1[C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH3:21])[C:17]=3[CH:22]=2)[C:3](=[O:23])[N:2]([CH3:1])[C:7]=1[C:8]([F:9])([F:10])[F:11]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24648Sulfuryl chlorideHCID 15477620HCID 15477620, compound

Product 1

HCID 22119889HCID 22119889, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-methyl-3-(3-methyl-1,2-benzisothiazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (1.00 g, 0.00293 mol), sulfuryl chloride (2.00 g 0.0148 mol) and 1,2-dichloroethane is stirred for five hours at reflux, cooled to room temperature, and diluted with methylene chloride. The resultant mixture is washed with saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain a residue. The residue is chromatographed on silica gel with ethyl acetate/hexanes to afford the title product as a white solid (0.350 g, 31.8%, mp 252-254° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. washThe resultant mixture is washed with saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue
  7. customThe residue is chromatographed on silica gel with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-149311686d794393a08f4471b9efeb2f
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

Loading…