Sulfuryl chloride → HCID 22119941, compound

HRID 1274637Notes

Reaction equation

HRID 1274637 reaction equation
[C:1]([C:4]1[C:8]2[CH:9]=[C:10]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])[CH:11]=[CH:12][C:7]=2[S:6][N:5]=1)(=[O:3])[CH3:2].S(Cl)([Cl:29])(=O)=O>C(Cl)(Cl)Cl.Cl.C(OCC)(=O)C.CCOCC>[Cl:29][CH2:2][C:1]([C:4]1[C:8]2[CH:9]=[C:10]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])[CH:11]=[CH:12][C:7]=2[S:6][N:5]=1)=[O:3]

Participants

7

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 22119925HCID 22119925, compound

Product 1

HCID 22119941HCID 22119941, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3-acetyl-1,2-benzisothiazol-5-yl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.570 g, 0.00154 mol) in chloroform is added sulfuryl chloride (0.350 ml, 0.00433 mol). The resultant mixture is stirred one hour at reflux. Concentrated hydrochloric acid (one drop) is added followed by sulfuryl chloride (1.05 ml, 0.0130 mol) and the resultant mixture is stirred three days at reflux. The mixture is cooled to room temperature, diluted with ethyl acetate and ether, washed with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to a solid. The resultant solid is chromatographed on silica gel with hexanes:ethyl acetate to afford a white solid. The solid is chromatographed on silica gel with chloroform to afford a white solid, which is recrystallized from ethyl acetate and hexanes to give the title compound as a white crystalline solid (mp 215-215° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. temperatureat reflux
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo to a solid
  6. customThe resultant solid is chromatographed on silica gel with hexanes
  7. customethyl acetate to afford a white solid
  8. customThe solid is chromatographed on silica gel with chloroform
  9. customto afford a white solid, which
  10. customis recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-da62a62f8ace47528b3016368e78e654
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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