2-(Furfurylthio)ethylamine → N-(2-(furan-2-ylmethylthio)ethyl)-4-methoxy-3-methylbenzamide

HRID 339386Notes

Reaction equation

HRID 339386 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[CH3:12].[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][S:19][CH2:20][CH2:21][NH2:22]>>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][S:19][CH2:20][CH2:21][NH:22][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH3:12])[CH:5]=1

Participants

3

Reactant 2

HCID 1189702-(Furfurylthio)ethylamineHCID 27595834-Methoxy-3-methylbenzoic Acid

Product 1

HCID 57527865N-(2-(furan-2-ylmethylthio)ethyl)-4-methoxy-3-methylbenzamideYield 58%

Procedure

Prepared in a similar manner as described in example 4 from 4-methoxy-3-methylbenzoic acid and 2-(furan-2-ylmethylthio)ethanamine. Yield 58%. 1H NMR (500 MHz, CDCl3) 2.23 (s, 3H), 2.76 (t, 2H, J=6.37 Hz), 3.59 (q, 2H, J=12.2 Hz), 3.76 (s, 2H), 3.86 (s, 3H), 6.22 (dd, 1H, J=3.49 Hz, J=2.67 Hz), 6.30 (dd, 1H, J=3.04 Hz, J=1.78 Hz), 6.46 (m, 1H, broad), 6.83 (d, 1H, J=8.51 Hz), 7.34 (dd, 1H, J=1.97 Hz, J=1 Hz), 7.56 (d, 1H, J=1.72 Hz), 7.61 (dd, 1H, J=8.53 Hz, J=2.25 Hz). MS (M+H, 306).

Workup

  1. customPrepared in a similar manner

Sources & evidence

ORD record
ord-d1b3a3c3c6ae4308b18a5aeced8718e2
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Reaction notes

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