Triethylamine → N-methoxy-N-methylthiophene-2-carboxamide

HRID 401172Notes

Reaction equation

HRID 401172 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.Cl.[CH3:10][NH:11][O:12][CH3:13].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[CH3:13][O:12][N:11]([CH3:10])[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 107002-Thiophenecarboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 3613942N-methoxy-N-methylthiophene-2-carboxamideYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of thiophene-2-carboxylic acid (2 g, 15.6 mmol), N,O-dimethylhydroxylamine hydrochloride (1.5 g, 15.6 mmol), EDCI (3.1 g, 15.6 mmol), HOBT (2.4 g, 15.6 mmol), Et3N (6.5 mL, 46.8 mmol) in DCM (30 mL) was stirred at room temperature for 4 hours. The mixture was concentrated in vacuo and purified by column to give N-methoxy-N-methylthiophene-2-carboxamide (1.8 g, yield 67%) as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by column

Sources & evidence

ORD record
ord-664b4bf423c44d01817c11a251e5dcf2
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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