Methanol → HCID 178515507, compound

HRID 1673016Notes

Reaction equation

HRID 1673016 reaction equation
COC(=O)[CH:4]([C:7]1[S:8][C:9]([Br:12])=[CH:10][CH:11]=1)[CH:5]=O.Cl.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][NH2:23].[CH3:24][OH:25]>Cl>[Br:12][C:9]1[S:8][C:7]([C:4]2[N:22]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[Cl:15])[N:23]=[C:24]([OH:25])[CH:5]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 86640017HCID 86640017, compound

Product 1

HCID 178515507HCID 178515507, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 3-(5-bromo-thiophen-2-yl-3-oxo-propionic acid methyl ester (2.0 g, 7.60 mmol) in 1.2 M HCl in MeOH (20 mL) was added 2-chlorophenylhydrazine hydrochloride (1.43 g, 7.98 mmol). The reaction mixture was heated to reflux for 4 hours and cooled off. The solvent was evaporated and the residue was purified by flash column chromatography with 10% ethyl acetate in hexane. The product 5-(5-bromo-thiophene-2-yl)-1-(2-chloro-phenyl)-1H-pyrazole-3-ol was recovered as a white solid (1.89 g, 70% yield. MS (ES): 355 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperaturecooled off
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash column chromatography with 10% ethyl acetate in hexane
  6. customThe product 5-(5-bromo-thiophene-2-yl)-1-(2-chloro-phenyl)-1H-pyrazole-3-ol was recovered as a white solid (1.89 g, 70% yield

Sources & evidence

ORD record
ord-50598560cfaf423aa24018dd8db473b0
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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