Methylamine → 2-Ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamide

HRID 985340Notes

Reaction equation

C([O:4][C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([CH2:13][CH3:14])[S:10][C:9]=2[CH:15]=1)(=O)C.[C:16](Cl)(=[O:20])C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:26][NH2:27]>>[CH3:26][NH:27][C:16]([C:12]1[C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:15][C:9]=2[S:10][C:11]=1[CH2:13][CH3:14])=[O:20]

Participants

Reactant 4

HCID 6329Methylamine

HCID 65578Oxalyl chloride

HCID 6451240Aluminum(III) Chloride

HCID 221435142-Ethyl-1-benzothiophen-6-yl acetate

Product 1

HCID 207677932-Ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamideYield 82%

Procedure

This material was prepared from 6-acetoxy-2-ethylbenzo[b]thiophene 134c (1.77 g, 8 mmole) by acylation with oxalyl chloride in the presence of AlCl3, followed by treatment with methylamine in a manner as previously described for example 1d to give a pale yellow solid (1.55 g, 82%). 1H NMR (DMSO-d6) δ9.57 (1H, s), 8.15 (1H, q, J=4.5 Hz), 7.48 (1H, d, J=8.6 Hz), 7.19 (1H, d, J=2.3 Hz), 6.84 (1H, dd, J=2.3, 8.6 Hz), 2.90 (2H, q, J=7.5 Hz), 2.78 (3H, d, J=4.5 Hz), 1.22 (3H, t, J=7.5 Hz).

Sources & evidence

ORD record: ord-fce61b695584488193bbf2c4826c0724
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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