Sulfuryl chloride → HCID 178470420, compound

HRID 585106Notes

Reaction equation

HRID 585106 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:13][CH:12]=2)[CH:10]=1)=[O:5])[CH3:2].S(Cl)([Cl:25])(=O)=O>ClCCl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:13][CH:12]=2)[C:10]=1[Cl:25])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178468652HCID 178468652, compound

Product 1

HCID 178470420HCID 178470420, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 25 mg (0.084 mmol) of the above-prepared 5-(2-phenyl-thiazol-5-yl)-2H-pyrazole-3-carboxylic acid ethyl ester in dichloromethane was added 23 mg (0.168 mmol) of sulfuryl chloride and allowed to stir overnight at room temperature. The solution was diluted with ethyl acetate, washed once with aqueous sodium bicarbonate, once with water once with brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using 7:93 ethyl acetate:hexanes as eluant to give 23 mg of the title compound (82%). 1H NMR (500 MHz, CDCl3) δ 8.39 (s, 1H) 7.94 (d, 2H) 7.40 (m, 2H) 4.40 (q, 2H) 1.38 (t, 3H).

Workup

  1. washwashed once with aqueous sodium bicarbonate, once with water once with brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by chromatography on silica gel using 7:93 ethyl acetate

Sources & evidence

ORD record
ord-f687c1b3d6c74fc29aee5658fead1e79
Source dataset
uspto-grants-2005_08
Patent number
US06930116B2

Reaction notes

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