3-Amino-1,2-propanediol → HCID 14700208, Verbindung

HRID 1651511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651511
CO[C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:12][C:7]=2[CH:6]=1)=[O:4].[OH:17][CH:18]([CH2:21][OH:22])[CH2:19][NH2:20]>CO>[OH:17][CH:18]([CH2:21][OH:22])[CH2:19][NH:20][C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([S:13]([NH2:16])(=[O:14])=[O:15])=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 735613-Amino-1,2-propanediolHCID 14700202Methyl 5-sulfamoylthieno[2,3-b]thiophene-2-carboxylate

Produkt 1

HCID 14700208HCID 14700208, VerbindungAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

5-Methoxycarbonylthieno[2,3-b]thiophene-2-sulfonamide (0.83 g., 3 mmoles) and 2,3-dihydroxypropylamine (1.37 g., 15 mmoles) were dissolved in hot methanol and refluxed for 48 hours. The reaction was worked up by evaporating the methanol in vacuo. Water (7 mL) was added followed by the dropwise addition of conc. HCl until strongly acidic (~1.8 pH). The product crystallized out and was collected, washed with water and dried to give 0.90 g of crude product. Recrystallization from nitromethane gave 0.73 g of 5-(N-2,3-dihydroxypropylcarbamoyl)thieno[2,3-b]thiophene-2-sulfonamide, m.p. 117°-118° C.

Aufarbeitung

  1. temperaturerefluxed for 48 hours
  2. customby evaporating the methanol in vacuo
  3. additionWater (7 mL) was added
  4. additionfollowed by the dropwise addition of conc. HCl until strongly acidic (~1.8 pH)
  5. customThe product crystallized out
  6. customwas collected
  7. washwashed with water
  8. customdried
  9. customto give 0.90 g of crude product
  10. customRecrystallization from nitromethane

Quellen und Nachweise

ORD-Eintrag
ord-7d9fc4a3d30a4aed8c45720ed3f55aad
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04929549

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