Hydrazine hydrate (1:1) → 4-(2-Amino-3-mercaptophenylsulfonamido)benzoic acid

HRID 2202411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202411
[S:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([S:10]([NH:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)(=[O:12])=[O:11])=[C:4]2[N:3]=C1.O.NN>CCO>[NH2:3][C:4]1[C:5]([SH:1])=[CH:6][CH:7]=[CH:8][C:9]=1[S:10]([NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)(=[O:11])=[O:12]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 904189724-(Benzo[d]thiazole-4-sulfonamido)benzoic acid

Produkt 1

HCID 904190184-(2-Amino-3-mercaptophenylsulfonamido)benzoic acidAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of 4-(benzo[d]thiazole-4-sulfonamido)benzoic acid (500 mg, 1.5 mmol) in 6 mL of EtOH was added hydrazine hydrate (479 mg, 15 mmol) at r.t. The reaction mixture was then stirred at 130° C. in microwave for 1.5 h. The resulting mixture was then cooled, and partitioned between water and EtOAc. The organic phase was washed with brine, dried over anhy. Na2SO4 and concentrated in vacuo to afford the title compound (449.0 mg). LC-MS: m/z 323.4 (M+H)+

Aufarbeitung

  1. temperatureThe resulting mixture was then cooled
  2. custompartitioned between water and EtOAc
  3. washThe organic phase was washed with brine
  4. customdried over anhy
  5. concentrationNa2SO4 and concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f758fce5219f408dacb7d617f7fdfb27
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365545B2

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