Acetic Acid → 4-Methyl-2,1,3-benzothiadiazol-5-amine

HRID 2378479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378479
[CH3:1][C:2]1[C:7]2=[N:8][S:9][N:10]=[C:6]2[CH:5]=[CH:4][C:3]=1[N+:11]([O-])=O.C(O)(=O)C.O>C1COCC1.[Fe]>[CH3:1][C:2]1[C:7]2=[N:8][S:9][N:10]=[C:6]2[CH:5]=[CH:4][C:3]=1[NH2:11]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 962WaterHCID 6764462,1,3-Benzothiadiazole, 4-methyl-5-nitro-

Produkt 1

HCID 41871374-Methyl-2,1,3-benzothiadiazol-5-amineAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Methyl-5-nitro-benzo[1,2,5]thiadiazole (1.4 g, 7.18 mmol) was dissolved in THF (10 mL), acetic acid (1 mL) and water (21 mL) and iron powder (1.4 g, 25.0 mmol, 325 Mesh) was added. The reaction mixture was heated at 80° C. for 1.5 h, cooled to rt and filtered though celite to remove the iron powder. The solution was extracted with CHCl3 (2×250 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give compound 839C (1.1 g) as a light brown solid.

Aufarbeitung

  1. temperaturecooled to rt
  2. filtrationfiltered though celite
  3. customto remove the iron powder
  4. extractionThe solution was extracted with CHCl3 (2×250 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a2b054b909f641c8b962990ec3a5cd42
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470797B2

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