Sulfuryl chloride → HCID 12082826, compound

HRID 966456Notes

Reaction equation

HRID 966456 reaction equation
[CH2:1]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[N:6]=1)[CH:2]([CH3:4])[CH3:3].S(Cl)([Cl:29])(=O)=O>C(Cl)Cl>[Cl:29][C:9]1[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[N:6][N:7]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[C:8]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 12082817HCID 12082817, compound

Product 1

HCID 12082826HCID 12082826, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the pyrazole prepared in Example 175 (0.15 g, 0.42 mmol) in CH2Cl2 (10 mL) was added an excess of sulfuryl chloride slowly at room temperature. The mixture was stirred at room temperature for 2 hours, quenched with water and the aqueous layer extracted three time with methylene chloride. The combined organic layers were dried over MgSO4 and concentrated to give an oil which was purified by flash chromatography on silica gel using 70:30 hexane/ethyl acetate as eluent to give the desired compound: HRMS m/z 389.0970 (calc'd for C19H20ClN3SO2, 389.0965).

Workup

  1. customquenched with water
  2. extractionthe aqueous layer extracted three time with methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customto give an oil which
  6. customwas purified by flash chromatography on silica gel using 70:30 hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-3251eac3f7884520a13f0f74fa7cf196
Source dataset
uspto-grants-2005_10
Patent number
US06951949B2

Reaction notes

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