4-Fluorobenzylamine → N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamide

HRID 1887250Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=O.[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1>>[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:16][C:7]([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])=[O:9])=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 673264-Fluorobenzylamine

HCID 902693-Methyl-2-thenoic acid

Product 1

HCID 5237273N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamideYield 94%

Procedure

Following the procedure as described in Preparation 18, making variations only as required to use 3-methylthiophene-2-carboxylic acid in place of 3-methylfuran-2-carboxylic acid to react with 4-fluorobenzylamine in place of benzylamine, N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamide was obtained as a colorless solid in 94% yield: 1H NMR (300 MHz, CDCl3) δ 7.37-7.26 (m, 3H), 7.08-7.00 (m, 2H), 6.90 (d, J=5.0 Hz, 1H), 6.09 (br s, 1H), 4.57 (d, J=5.8 Hz, 2H), 2.52 (s, 3H); MS (ES+) m/z 250.2 (M+1).

Workup

customas described in Preparation 18

Sources & evidence

ORD record: ord-dd30d6c32d244d9086a7cf84cb1c5913
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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