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

HRID 1744902노트

반응식

HRID 1744902 반응식
[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]

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 11105777HCID 11105777, 화합물HCID 178418306HCID 178418306, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ba64bfb7471c43ee90766f6085678886
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07019027B2

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