Tetrahydrofuran → 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid

HRID 504614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504614
[CH3:1][N:2]([S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([O:14]CC)=[O:13])=[CH:8]2.[OH-].[Na+].O1CCCC1>CO>[CH3:1][N:2]([S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]2

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57475952ethyl 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate

Produkt 1

HCID 574759517-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acidAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of ethyl 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (0.40 g), 8N aqueous sodium hydroxide solution (0.40 ml), tetrahydrofuran (5 ml) and methanol (5 ml) was stirred at 60° C. for 1 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were collected by filtration, washed with water, and dried to give the title compound (0.35 g, yield 91%) as colorless crystals. melting point >240° C. (decomposition).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7400a342216c4d2abb890cec904bbebe
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07777047B2

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