N-Methylaniline → Methyl 4-(methylphenylamino)-5-methylthiothiophene-2-carboxylate

HRID 2298683Notes

Reaction equation

HRID 2298683 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=1[CH3:7].[CH3:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:12][N:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=1[CH3:7]

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 86583861Methyl 4-bromo-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758693Methyl 4-(methylphenylamino)-5-methylthiothiophene-2-carboxylateYield 22.2%

Procedure

A stirred suspension of 100 mg (0.374 mmol) of methyl 4-bromo-5-methylthiothiophene-2-carboxylate and 72 μL (0.487 mmol, 1.3 eq) of N-methylaniline (Aldrich Chemical Co., Milwaukee, Wis.) was treated in a manner similar to Example 245, step (a) to give 23 mg of the title compound (21%) as a yellow oil. 1H-NMR (CDCl3, 400 MHz) δ7.61 (s, 1H), 7.26-6.68 (m, 5H), 3.89 (s, 3H), 3.25 (s, 3H), 2.50 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C14H15NO2S2, 294.1 (M+H), found 294.3.

Workup

  1. additionwas treated in a manner similar to Example 245, step (a)

Sources & evidence

ORD record
ord-196e1bd6edbd4a8e93ffdbde9c03a6c5
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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