Benzoyl chloride → 3-Benzoyl-4,5-dimethylthiophene-2-carboxylic acid methylamide

HRID 1744902ノート

反応式

HRID 1744902 の反応式
[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]([CH3:11])=[C:8]([CH3:10])[CH:9]=1)=[O:4].C([Li])(C)(C)C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]([CH3:11])=[C:8]([CH3:10])[C:9]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:4]

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 11105777HCID 11105777、化合物HCID 178418306HCID 178418306、化合物

生成物 1

HCID 110439513-Benzoyl-4,5-dimethylthiophene-2-carboxylic acid methylamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 10 (0.40 g, 2.37 mmole) in 20 mL dry THF was cooled to −70° C. and stirred during the addition of t-butyllithium (5.21 mmole). After 30 minutes of stirring benzoyl chloride (0.42 g=0.35 mL, 3 mmole) was added and the mixture was warmed to room temperature. Workup consisted of quenching the reaction with saturated aqueous NH4Cl and extraction of product into ethyl acetate. The extract was dried over MgSO4, evaporated and product purified by chromatography on silica gel eluted with hexane-ethyl acetate 1:1. Yield 0.356 g, 55% 1H NMR(CDCl3) δ: 1.83 (s, 3H, CH3), 2.37 (s, 3H, CH3), 2.79 (d, 3H, NHCH3), 6.58 (br s, 1H, NH), 7.42–7.78 (m, 5H, ArH).

後処理

  1. customof quenching
  2. customthe reaction
  3. extractionwith saturated aqueous NH4Cl and extraction of product into ethyl acetate
  4. dry with materialThe extract was dried over MgSO4
  5. customevaporated
  6. customproduct purified by chromatography on silica gel
  7. washeluted with hexane-ethyl acetate 1:1

出典と根拠

ORDレコード
ord-ba64bfb7471c43ee90766f6085678886
出典データセット
uspto-grants-2006_03
特許番号
US07019027B2

反応ノート

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