Methyl 3-(aminosulfonyl)-2-thiophenecarboxylate → 2-(Hydroxymethyl)thiophene-3-sulfonamide

HRID 1252352

Reaktionsgleichung

Reaktionsgleichung von HRID 1252352
[NH2:1][S:2]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10](OC)=[O:11])(=[O:4])=[O:3].[BH4-].[Li+]>O1CCCC1>[OH:11][CH2:10][C:6]1[S:7][CH:8]=[CH:9][C:5]=1[S:2]([NH2:1])(=[O:4])=[O:3]

Komponenten

4

Edukt 2

HCID 101012Methyl 3-(aminosulfonyl)-2-thiophenecarboxylateHCID 4148881Lithium borohydride

Produkt 1

HCID 142549372-(Hydroxymethyl)thiophene-3-sulfonamideAusbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 5.0 g of methyl 3-aminosulfonylthiophene-2-carboxylate in 200 mL of tetrahydrofuran was added 0.75 g of lithium borohydride. After heating at reflux for two hours the reaction was quenched with water and acidified with concentrated hydrochloric acid. The desired product was then extracted into methylene chloride which was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 1.8 g of a yellow solid, m.p. 85°-89°.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureat reflux for two hours the reaction
  3. customwas quenched with water
  4. extractionThe desired product was then extracted into methylene chloride which
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c05cdcf7574e4c4cb07a343f8ed48be9
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04743290

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