Methylamine → 6-Methoxy-N-methyl-2-(1-methylethyl)-3-benzofurancarboxamide

HRID 985204Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[O:9][C:5]=2[CH:4]=1.[C:15](Cl)(=[O:19])C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:25][NH2:26]>>[CH3:25][NH:26][C:15]([C:7]1[C:6]2[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[O:9][C:8]=1[CH:10]([CH3:11])[CH3:12])=[O:19]

Participants

Reactant 4

HCID 6329Methylamine

HCID 65578Oxalyl chloride

HCID 6451240Aluminum(III) Chloride

HCID 107977526-Methoxy-2-(1-methylethyl)benzofuran

Product 1

HCID 207678016-Methoxy-N-methyl-2-(1-methylethyl)-3-benzofurancarboxamideYield 60%

Procedure

Example 15(b) was prepared from 6-methoxy-2-(1-methylethyl)benzofuran 15a (263 mg, 1.36 mmole) by acylation with oxalyl chloride in the presence of AlCl3, followed by treatment with methylamine in a manner as previously described for example 1c to give 200 mg (60%) of an off-white solid. 1H NMR (DMSO-d6) δ7.83 (1H, d, J=4.8 Hz), 7.56 (1H, d, J=8.8 Hz), 7.20 (1H, d, J=2.3 Hz), 6.89 (1H, dd, J=2.3, 8.8 Hz), 3.78 (3H, s), 3.68-3.61 (1H, m), 2.78 (3H, d, J=4.8 Hz), 1.26 (6H, d, J=6.8 Hz).

Sources & evidence

ORD record: ord-e7f8e85574a146b895a86b654ce8a628
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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