3-Chloroaniline → Methyl 4-[(3-chlorophenyl)amino]-5-methylthiothiophene-2-carboxylate

HRID 2298682Notes

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].[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16]>>[Cl:12][C:13]1[CH:14]=[C:15]([NH:16][C:2]2[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=2[CH3:7])[CH:17]=[CH:18][CH:19]=1

Participants

Reactant 2

HCID 79323-Chloroaniline

HCID 86583861Methyl 4-bromo-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86758692Methyl 4-[(3-chlorophenyl)amino]-5-methylthiothiophene-2-carboxylateYield 52.8%

Procedure

A stirred suspension of 80 mg (0.299 mmol) of methyl 4-bromo-5-methylthiothiophene-2-carboxylate and 41 μL (0.389 mol, 1.3 eq) of 3-chloroaniline (Aldrich, Milwaukee, Wis.) was treated in a manner similar to Example 241, step (b) to give 47 mg of the title compound (50%) as a yellow oil. 1H-NMR (CDCl3, 400 MHz) δ7.75 (s, 1H), 7.23-6.89 (m, 4H), 6.10 (s, 1H), 3.89 (s, 3H), 2.42 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C13H2NO12S2Cl, 314.0 (M+H), found 314.1.

Workup

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

Sources & evidence

ORD record: ord-f6e6e30a61dd45a9982690ff0c9a2747
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492403B1

Reaction notes

Loading…