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

HRID 736255ノート

反応式

HRID 736255 の反応式
[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

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 12185Ethyl ThioglycolateHCID 57434727HCID 57434727、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

1.19 g (3.81 mmol) of 3,5-dibromo-1-(1-ethoxyethyl)-1H-pyrazole-4-carboxaldehyde are introduced with stirring into 50 mL 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 mL (3.81 mmol) of ethyl 2-mercaptoacetate. The reaction mixture is then refluxed for 2 hours, and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 60 mL of water and 60 mL 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 pale yellow oil that crystallizes to give cream-colored crystals melting at 69° C.

後処理

  1. temperatureThe reaction mixture is then refluxed for 2 hours
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. custom60 mL 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)

出典と根拠

ORDレコード
ord-88ca9d07b3da498c976ceaf3c284ad3d
出典データセット
uspto-grants-2009_09
特許番号
US07595320B2

反応ノート

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