Aniline → Methyl 5-methyl-4-(phenylamino)thiophene-2-carboxylate

HRID 2298684Notes

Reaction equation

HRID 2298684 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1Br.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 18536848Methyl 4-bromo-5-methylthiophene-2-carboxylate

Product 1

HCID 18537139Methyl 5-methyl-4-(phenylamino)thiophene-2-carboxylateYield 16%

Procedure

A stirred suspension of 400 mg (1.7 mmol) methyl 5-methyl-4-bromo-thiophene-2-carboxylate and 192 μL (2.1 mmol, 1.25 eq) of aniline (Aldrich, Milwaukee, Wis.) was treated in a manner similar to Example 241, step (b) to give 66 mg of the title compound (16%) as a brown glass. 1H-NMR (DMSO-d6, 400 MHz) δ7.70 (s, 1H), 7.56 (s, 1H), 7.17 (m, 2H), 6.72 (m, 3H), 3.79 (s, 3H), 2.31 (s, 3H). Mass spectrum (MALDI, gentisic acid matrix, m/z): Calcd. for C13H13NO2S, 248.1 (M+H), found 247.5.

Workup

  1. additionwas treated in a manner similar to Example 241, step (b)

Sources & evidence

ORD record
ord-6972a8aa90b842058e74d24885bf01fa
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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