Octylamine → HCID 68154461, compound

HRID 2410238Notes

Reaction equation

HRID 2410238 reaction equation
[S:1]1[CH:5]=[C:4]2[C:6]([O:8][C:9](=[O:10])[C:3]2=[CH:2]1)=[O:7].[CH2:11]([NH2:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1(C)C=CC=CC=1>[CH2:11]([NH:19][C:6]([C:4]1[C:3]([C:9]([OH:8])=[O:10])=[CH:2][S:1][CH:5]=1)=[O:7])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 8143OctylamineHCID 3156081H,3H-Thieno[3,4-c]furan-1,3-dione

Product 1

HCID 68154461HCID 68154461, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The anhydride was subsequently dissolved in toluene (320 mL) in a 500 mL flask, followed by the addition of n-octylamine (6.72 g, 52.02 mmol, 8.6 mL). The resulting reaction mixture was subsequently refluxed over a period of 24 h. The reaction mixture was allowed to cool and was subsequently concentrated affording 4-octylcarbamoylthiophene-3-carboxylic acid as a solid. The acid was dissolved in thionyl chloride (SOCl2) (270 mL) and refluxed over a period of 4 hours. The reaction mixture was cooled down and subsequently concentrated to dryness. The residue was purified by column chromatography using methylene dichloride:hexanes (2:1) as the eluant to afford the title compound as a pure white solid (5.2 g, yield 57%): mp: 120-122° C.; GC-Ms: 265; 1H NMR (400 MHz, CDCl3, ppm) δ:7.8(s, 2H), 3.62-3.59 (t, 2H), 1.64-1.62(m, 2H), 1.26(m, 10H), 0.87-0.85(m, 3H); 13C NMR (100 MHz, CDCl3, ppm) δ: 162.4, 136.7, 125.2, 37.9, 31.7, 29.2 (2C), 28.4, 26.8, 22.4, 14.1.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas subsequently refluxed over a period of 24 h
  3. temperatureto cool
  4. concentrationwas subsequently concentrated

Sources & evidence

ORD record
ord-b8bbc6900a664895ac5da30c02513ab4
Source dataset
uspto-grants-2014_08
Patent number
US08816035B2

Reaction notes

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