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3-Thiophencarboxamide,N-methyl- → HCID 10244631、化合物

HRID 1437141
ノート
印刷プレビュー

反応式

HRID 1437141 の反応式
[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)=[O:4].O[CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15]>S(=O)(=O)(O)O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[C:8]([CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[S:7][CH:6]=1)=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 8195533-Thiophencarboxamide,N-methyl-HCID 30849312,2,2-Trifluoro-N-(hydroxymethyl)acetamide

生成物 1

HCID 10244631HCID 10244631、化合物

試薬・触媒・溶媒 3

HCID 1118Sulfuric Acid溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒2 回

反応条件

温度
20 °C

実験手順

To suspension of N-methyl-3-thiophenecarboxamide (1.12 g) (prepared according to J. Org. Chem. (1976), 41(23), 3668-74) in concentrated aqueous sulphuric acid (25 ml) at 0-5° C. was added N-(hydroxymethyl)trifluoroacetamide (1.134 g). The suspension was allowed to warm to 20° C. and stirred for 2 h. The mixture was poured onto ice (150 g) and diluted with ethyl acetate (200 ml). The biphase mixture was diluted with saturated sodium hydrogen carbonate (200 ml) and treated with sodium hydrogen carbonate (21 g). The phases were separated and the organic phase washed with saturated sodium hydrogen carbonate (150 ml×2). The combined aqueous phases were extracted with ethyl acetate (100 ml). The combined organic extracts were concentrated in vacuo. The residue was pre-absorbed onto silica and purified by biotage (90 g) eluting with 1:1 to 0:1 cyclohexane:ethyl acetate to give the title compound as a white solid (0.7129).

後処理

  1. additionThe mixture was poured onto ice (150 g)
  2. customThe phases were separated
  3. washthe organic phase washed with saturated sodium hydrogen carbonate (150 ml×2)
  4. extractionThe combined aqueous phases were extracted with ethyl acetate (100 ml)
  5. concentrationThe combined organic extracts were concentrated in vacuo
  6. customThe residue was pre-absorbed onto silica
  7. custompurified by biotage (90 g)
  8. washeluting with 1:1 to 0:1 cyclohexane

出典と根拠

ORDレコード
ord-be5173694d8d4c139d62c84e87399bc1
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07622464B2

反応ノート

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