Hydrochloric Acid → HCID 22227967, compound

HRID 1744678Notes

Reaction equation

HRID 1744678 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23][CH2:24][CH2:25][CH2:26][OH:27])=[C:19]([C:28]#[N:29])[CH:18]=3)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23][CH2:24][CH2:25][CH2:26][O:27][S:31]([CH3:30])(=[O:33])=[O:32])=[C:19]([C:28]#[N:29])[CH:18]=3)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 22227888HCID 22227888, compound

Product 1

HCID 22227967HCID 22227967, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(4-chlorophenyl)-N-[3-cyano-4-(3-hydroxypropylthio)phenyl]-5-methylpyrazole-4-carboxamide (1.8 g) and methanesulfonyl chloride (0.5 ml) in pyridine (20 ml) was stirred overnight. To the reaction mixture was added aqueous hydrochloric acid solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: chloroform:methanol=50:1) to give 1-(4-chlorophenyl)-N-[3-cyano-4-(3-methanesulfonyloxypropylthio)phenyl]-5-methylpyrazole-4-carboxamide (1.2 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (mobile phase: chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-51b5fa0e6ee249a78d859da91fb39d9b
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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