3-Methoxyaniline → N-(3-methoxyphenyl)thiophene-2-carboxamide

HRID 38238Notes

Reaction equation

HRID 38238 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:14][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 108243-MethoxyanilineHCID 789282-Thiophenecarbonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 790310N-(3-methoxyphenyl)thiophene-2-carboxamideYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

According to Scheme 1 Method A: A solution of thiophene-2-carbonyl chloride (2.92 mmol, 0.31 mL) in DCM (1 mL) was added to solution of 3-methoxyaniline (2.44 mmol, 0.27 mL) and DIEA (4.87 mmol, 0.87 mL) in DCM (4 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 hour. The organic phase was washed with HCl 1 M solution, then with a saturated solution of NaHCO3, was dried over MgSO4, was filtered and was concentrated under reduced pressure to yield N-(3-methoxyphenyl)thiophene-2-carboxamide (1.71 mmol, 0.40 g, 70%) as a white solid.

Workup

  1. washThe organic phase was washed with HCl 1 M solution
  2. dry with materialwith a saturated solution of NaHCO3, was dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-e69d8d13c7004571a8e87e764f1f63c3
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Reaction notes

Loading…