Hydrochloric Acid → (E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoic acid

HRID 350323ノート

反応式

HRID 350323 の反応式
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:37]=[CH:36][C:17]([CH2:18][N:19]4[CH:23]=[C:22](/[CH:24]=[CH:25]/[C:26]([O:28]CC)=[O:27])[C:21]([C:31]5[S:32][CH:33]=[CH:34][CH:35]=5)=[N:20]4)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:37]=[CH:36][C:17]([CH2:18][N:19]4[CH:23]=[C:22](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])[C:21]([C:31]5[S:32][CH:33]=[CH:34][CH:35]=5)=[N:20]4)=[CH:16][CH:15]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69423225ethyl(E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoate

生成物 1

HCID 69422351(E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoic acid収率 82%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

After a mixture of ethyl(E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoate (1.25 g), 1N aqueous sodium hydroxide solution (5 ml), tetrahydrofuran (5 ml), and ethanol (5 ml) was stirred at 50° C. for 2 hours, 1N hydrochloric acid (5 ml) was added to the mixture, and then the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The resulting colorless crystals were collected by filtration to obtain (E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoic acid (970 mg, yield 82%). This was recrystallized from ethyl acetate-hexane. Melting point: 137˜138° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe resulting colorless crystals were collected by filtration

出典と根拠

ORDレコード
ord-20e6165d43164e049264e20816c8b707
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

反応ノート

読み込み中…