Pyrrole-2-carboxaldehyde → HCID 136495275, compound

HRID 1485907Notes

Reaction equation

HRID 1485907 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH3:8][S:9][CH2:10][CH2:11][NH2:12]>>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[N:12][CH2:11][CH2:10][S:9][CH3:8]

Participants

3

Reactant 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 87697(2-(Methylthio)ethyl)amine

Product 1

HCID 136495275HCID 136495275, compoundYield 98.7%

Procedure

Replicate the preparation of the ligand used in Ex. 7 except use 0.928 g (9.758 mmol) of the pyrrole-2-carbaldehyde and 0.999 mL (10.734 mmol, p=0.980 gcm−3) of 2-(methylthio)ethylamine instead of N1,N1-dimethylethane-1,2-diamine to give 1.62 g (98%) of N-((1H-pyrrol-2-yl)methylene)-2-(methylthio)ethanamine as a pale yellow oil, which is analytically pure by GC-MS & 1H-NMR: 1H NMR (400 MHz, CDCl3) δ 9.45 (s, br, 1H), 7.99 (s, 1H), 6.78 (s, 1H), 6.40 (d, J=1.9 Hz, 1H), 6.14 (s, 1H), 3.64 (t, J=6.9 Hz, 2H), 2.66 (t, J=6.9 Hz, 2H), 2.04 (s, 3H).

Workup

  1. customthe preparation of the ligand

Sources & evidence

ORD record
ord-8eaad608664a4e2d94077d9e3d9c21f2
Source dataset
uspto-grants-2016_08
Patent number
US09422375B2

Reaction notes

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