2-Methoxyethylamine → Methyl 4,7-dihydro-5-(2-methoxyethyl)amino-4,7-dioxobenzo[b]thiophene-2-carboxylate

HRID 1582185Notes

Reaction equation

HRID 1582185 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[O:6]=[C:7]1[C:15]2[CH:14]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[S:12][C:11]=2[C:10](=[O:20])[CH:9]=[CH:8]1>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:8]1[C:7](=[O:6])[C:15]2[CH:14]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[S:12][C:11]=2[C:10](=[O:20])[CH:9]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 507039Methyl 4,7-dioxobenzothiophene-2-carboxylate

Product 1

HCID 12987499Methyl 4,7-dihydro-5-(2-methoxyethyl)amino-4,7-dioxobenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxyethylamine (1.6 ml) was added to a solution of methyl 4,7-dihydro-4,7-dioxobenzo[b]thiophene-2-carboxylate (2.4 g) in tetrahydrofuran (100 ml) and the mixture was stirred at room temperature for 27 hours. After evaporation of the solvent, the residue was purified by silica gel column chromatography (elution with chloroform) to give methyl 4,7-dihydro-5-(2-methoxyethyl)amino-4,7-dioxobenzo[b]thiophene-2-carboxylate (1.5 g) as a yellow powder.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by silica gel column chromatography (elution with chloroform)

Sources & evidence

ORD record
ord-2e37fe5b0f2046879bc553a1533a4612
Source dataset
uspto-grants-2004_05
Patent number
US06734203B2

Reaction notes

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