Sodium Chloride → N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamine

HRID 1363236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363236
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([N+:16]([O-])=O)[CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C1COCC1.O.CO>[NH2:16][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14]

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 59705030(4-Fluoro-2-nitro-phenyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 24688763N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-fluoro-2-nitrophenylcarbamate (0.34 g) in THF (30 mL) was added a premixed solution of sodium hydrosulfite (2 g) and sodium bicarbonate (1 g) in water (50 mL). MeOH (10 mL) was also added to aid solution of the mixture, which was stirred at room temperature for 30 min, when sodium chloride was added to saturate the solution. The resultant mixture was extracted with EtOAc (2×). The combined organics were dried, filtered and evaporated to yield the titled compound (quant) that was used as such for the next step. 1H-NMR (300 MHz, CDCl3) δ 7.5 (dd, 1H), 6.6 (dd, 1H), 6.5 (m, 1H), 6.4 (br 1H), 4.7 (br 2H), 1.5 (s, 9H); 19F δ −119 ppm; MH+=227 (minor) 127 (-BOC), 171 (-tBu).

Aufarbeitung

  1. concentrationto saturate the solution
  2. extractionThe resultant mixture was extracted with EtOAc (2×)
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-bb595cff459c4a8084e285714a076a0f
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884109B2

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