Sodium Carbonate → ethyl 3-bromo-1-(1-ethoxyethyl)-1H-thieno[2,3-c]pyrazole-5-carboxylate

HRID 1363067Notes

Reaction equation

HRID 1363067 reaction equation
[Br:1][C:2]1[C:6]([CH:7]=O)=[C:5](Br)[N:4]([CH:10]([O:12][CH2:13][CH3:14])[CH3:11])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[SH:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(O)C>[Br:1][C:2]1[C:6]2[CH:7]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:21][C:5]=2[N:4]([CH:10]([O:12][CH2:13][CH3:14])[CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12185Ethyl ThioglycolateHCID 57434727HCID 57434727, compound

Product 1

HCID 57487832ethyl 3-bromo-1-(1-ethoxyethyl)-1H-thieno[2,3-c]pyrazole-5-carboxylateYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.19 g (3.81 mmol) of 3,5-dibromo-1-(1-ethoxyethyl)-1H-pyrazole-4-carboxaldehyde are introduced with stirring into 50 cm3 of ethanol under an argon atmosphere, at a temperature in the region of 20° C., followed by addition of 0.4 g (3.81 mmol) of sodium carbonate and 0.42 cm3 (3.81 mmol) of ethyl 2-mercaptoacetate. The reaction mixture is then refluxed for 2 hours, and concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 60 cm3 of water and 60 cm3 of dichloromethane, and the phases are separated by settling. The organic phase is dried over magnesium sulfate and then concentrated to dryness under reduced pressure (2.7 kPa). 1.17 g of ethyl 3-bromo-1-(1-ethoxyethyl)-1H-thieno[2,3-c]pyrazole-5-carboxylate are thus obtained in the form of a clear yellow oil that crystallizes to give cream-colored crystals melting at 69° C.

Workup

  1. temperatureThe reaction mixture is then refluxed for 2 hours
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. custom60 cm3 of dichloromethane, and the phases are separated
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-8c5748c96f0a49ae8a225f4cc8a92926
Source dataset
uspto-grants-2011_02
Patent number
US07884123B2

Reaction notes

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