Thionyl Chloride → HCID 57562646, compound

HRID 1725466Notes

Reaction equation

HRID 1725466 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:14]=[C:13]([CH3:15])[NH:12][N:11]=2)[CH:6]=[CH:5][CH:4]=1.S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:18][CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:14]=[C:13]([CH3:15])[NH:12][N:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 57562667HCID 57562667, compound

Product 1

HCID 57562646HCID 57562646, compoundYield 114.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

68 mg (340 μmol) of 3-(6-hydroxymethylpyridin-2-yl)amino-5-methyl-1H-pyrazole was dissolved in 4 mL of a 6:1 mixed solvent of chloroform and dimethylformamide. Under cooling on an ice bath, 250 μL (3.4 mmol) of thionyl chloride was added thereto. After stirring at room temperature for 18 hours, the reaction solution was concentrated. The resulting residue was purified by a silica gel thin-layer chromatography to give 87 mg of a brown oil. This oil was used as it was for the next reaction.

Workup

  1. temperatureUnder cooling on an ice bath
  2. concentrationthe reaction solution was concentrated
  3. customThe resulting residue was purified by a silica gel thin-layer chromatography

Sources & evidence

ORD record
ord-0dcfb2ad734b43aba898397abacedb7d
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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