Hydrazine hydrate (1:1) → tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

HRID 62667

Reaktionsgleichung

Reaktionsgleichung von HRID 62667
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([O-])=O.O.NN>CO>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 59736984tert-Butyl 2-nitro-4-(thiophen-2-yl)phenylcarbamate

Produkt 1

HCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of tert-butyl (2-nitro-4-(thiophen-2-yl)phenyl)carbamate (1.6 g, 4.99 mmol, 1 eq.) in methanol (20 mL) was added hydrazine hydrate (14 mL) and ferric chloride (0.05 g, 0.3 mmol, 0.06 eq.). The resulting mixture was warmed to 60° C. and stirred for 2 h. The reaction was then filtered through Celite, the solids were washed with MeOH. The filtrate was concentrated under reduced pressure. Water was added to the residue and the suspension was stirred for 1 h. The obtained solid was filtered, washed with hexanes then dried to yield tert-butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (1.2 g, 83% yield).

Aufarbeitung

  1. filtrationThe reaction was then filtered through Celite
  2. washthe solids were washed with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. stirringthe suspension was stirred for 1 h
  6. filtrationThe obtained solid was filtered
  7. washwashed with hexanes
  8. customthen dried

Quellen und Nachweise

ORD-Eintrag
ord-b1815fdfd6c64e5a97cd19b00096e39b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447030B2

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