Dodecylamine → 5-Dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

HRID 2410240Notes

Reaction equation

[S:1]1[CH:5]=[C:4]([C:6](O)=[O:7])[C:3]([C:9]([OH:11])=O)=[CH:2]1.[CH2:12]([NH2:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>>[CH2:12]([N:24]1[C:9](=[O:11])[C:3]2=[CH:2][S:1][CH:5]=[C:4]2[C:6]1=[O:7])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Reactant 2

HCID 13583Dodecylamine

HCID 255853Thiophene-3,4-dicarboxylic acid

Product 1

HCID 592879495-Dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dioneYield 55%

Procedure

The title compound was synthesized as described hereinabove using thiophene-3,4-dicarboxylic acid (10.00 g, 58.08 mmol) and 1-dodecylamine (16.14 g, 87.12 mmol) to afford 10.27 g of the title product as a white solid (Y=55%). 1H NMR (400 MHz, CDCl3, ppm) δ: 7.80 (s, 2H); 3.60 (t, 2H, J=7.3 Hz); 1.65-1.62 (m, 2H); 1.30-1.24 (m, 18H); 0.87 (t, 3H, J=6.5 Hz); 13C NMR (100 MHz, CDCl3, ppm) δ: 162.92; 136.91; 125.71; 38.75; 32.15; 29.87; 29.85; 29.81; 29.75; 29.59; 29.45; 28.72; 27.12; 22.93; 14.39.

Workup

customThe title compound was synthesized

Sources & evidence

ORD record: ord-0146c80f6d8a48bca2db2c8ad44ffe56
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816035B2

Reaction notes

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