Thionyl Chloride → HCID 57562646, compound

HRID 1172409Notes

Reaction equation

HRID 1172409 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-12e793e9000946e2bd6e1e4b6b3ea231
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

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