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

HRID 2178056Notes

Reaction equation

HRID 2178056 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-595d1f0a1fa34a12a793e0a7bc8476e2
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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