Triethylamine → 2-(2-Methoxybenzamido)-4-methylthiophene-3-carboxamide

HRID 333709Notes

Reaction equation

HRID 333709 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8].CCN(CC)CC.CN(C1C=CC=CN=1)C.[CH3:27][O:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>C(Cl)Cl.O>[CH3:27][O:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8])=[O:32]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 889692-Methoxybenzoyl chlorideHCID 2938102-Amino-4-methylthiophene-3-carboxamide

Product 1

HCID 590266232-(2-Methoxybenzamido)-4-methylthiophene-3-carboxamideYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-amino-4-methylthiophene-3-carboxamide (0.47 g, 3 mmol), Et3N (0.46 mL, 3.3 mmol), and dimethylaminopyridine (0.073 g, 0.64 mmol) in CH2Cl2 (10.0 mL) was cooled in an ice bath, and 2-methoxybenzoyl chloride (513 mg, 3.0 mmol) was added dropwise to this mixture. The reaction was stirred for 1 h, and water (20 mL) was added. The insoluble solids were filtered, and the layers were separated. The organic layer was dried and the solvent removed under vacuum to give a residue which was purified with silica gel using EtOAc-hexanes to give 2-(2-methoxybenzamido)-4-methylthiophene-3-carboxamide (0.38 g, 44% yield). LC/MS: m/z 291.1 (M+H)+ at 2.59 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. filtrationThe insoluble solids were filtered
  2. customthe layers were separated
  3. customThe organic layer was dried
  4. customthe solvent removed under vacuum
  5. customto give a residue which
  6. customwas purified with silica gel

Sources & evidence

ORD record
ord-faf2010a747443c1b293ef4201ce1c77
Source dataset
uspto-grants-2014_11
Patent number
US08883781B2

Reaction notes

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