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

HRID 1744902Notes

Reaction equation

HRID 1744902 reaction equation
[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]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11105777HCID 11105777, compoundHCID 178418306HCID 178418306, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ba64bfb7471c43ee90766f6085678886
Source dataset
uspto-grants-2006_03
Patent number
US07019027B2

Reaction notes

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