Water → Thiophene-2,5-dicarboxylic acid bis-[(1,3-benzodioxol-5-ylmethyl)-amide]

HRID 583754

Reaktionsgleichung

Reaktionsgleichung von HRID 583754
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].[S:13]1[C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=[C:14]1C(O)=O.[CH2:24]([NH2:34])[C:25]1[CH:33]=[CH:32][C:31]2[O:30][CH2:29][O:28][C:27]=2[CH:26]=1.[OH2:35]>CN(C)C=O>[O:30]1[C:31]2[CH:32]=[CH:33][C:25]([CH2:24][NH:34][C:18]([C:17]3[S:13][C:14]([C:1]([NH:8][CH2:12][C:11]4[CH:24]=[CH:25][C:26]5[O:35][CH2:29][O:28][C:27]=5[CH:31]=4)=[O:2])=[CH:15][CH:16]=3)=[O:20])=[CH:26][C:27]=2[O:28][CH2:29]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 202732,5-Thiophenedicarboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 75799Benzo-1,3-dioxole-5-methylamine

Produkt 1

HCID 10173561Thiophene-2,5-dicarboxylic acid bis-[(1,3-benzodioxol-5-ylmethyl)-amide]

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1,1′-Carbonyldiimidazole (1.2 g, 7.4 mmol) was added to a stirred solution of 2,5-thiophene-dicarboxylic acid (0.5 g, 3.0 mmol) in dimethylformamide (25 mL) under an inert atmosphere, and the mixture was heated to 55° C. to 60° C. After 30 minutes, the mixture was allowed to cool and piperonylamine (1.05 g, 6.7 mmol) was added. The mixture was reheated to 55° C. to 60° C. After 3 hours, the mixture was allowed to cool, and was poured into water (250 mL), and the aqueous mixture was stirred. After several hours, the precipitate was filtered off, rinsed with water, and dried to afford 1.2 g of thiophene-2,5-dicarboxylic acid bis-[(1,3-benzodioxol-5-ylmethyl)-amide]. Recrystallization of a sample from ethanol gave product with a mp 207-209° C.

Aufarbeitung

  1. temperaturethe mixture was heated to 55° C. to 60° C
  2. temperatureto cool
  3. customwas reheated to 55° C. to 60° C
  4. waitAfter 3 hours
  5. temperatureto cool
  6. waitAfter several hours
  7. filtrationthe precipitate was filtered off
  8. washrinsed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5ec48cff01844ec380618709bc2ece9a
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924276B2

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