2-Methoxyaniline → HCID 86758691, compound

HRID 2298681Notes

Reaction equation

HRID 2298681 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][O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16]>>[CH3:12][O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][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 70002-MethoxyanilineHCID 86583861Methyl 4-bromo-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758691HCID 86758691, compoundYield 68.9%

Procedure

A stirred suspension of 103 mg (0.386 mmol) of methyl 4-bromo-5-methylthiothiophene-2-carboxylate and 57 mg (0.46 mmol, 1.2 eq) of 2-methoxyaniline (Aldrich, Milwaukee, Wis.) was treated in a manner similar to Example 241, step (b) to give 78 mg the title compound (65%) as a yellow oil. 1H-NMR (CDCl3, 400 MHz) δ7.82 (s, 1H), 7.12-6.52 (m, 4H), 6.52 (s, 1H), 3.92 (s, 3H), 3.87 (s, 3H), 2.40 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C14H15NO3S2, 310.1 (M+H), found 310.2.

Workup

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

Sources & evidence

ORD record
ord-e5b16fe58d7b4a15b197a5b2a0c246be
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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