Acetic Acid → 5-Amino-3-(6-methoxy-m-tolyl)-1,2-benzisothiazole

HRID 277355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277355
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[C:14]3[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=[CH:18][C:13]=3[S:12][N:11]=2)=[CH:5][CH:4]=1.C(O)(=O)C>[Fe].C(OCC)(=O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[S:12][N:11]=[C:10]([C:6]3[CH:7]=[C:8]([CH3:9])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:14]=2[CH:15]=1

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 698321503-(6-Methoxy-m-tolyl)-5-nitro-1,2-benzisothiazole

Produkt 1

HCID 698320455-Amino-3-(6-methoxy-m-tolyl)-1,2-benzisothiazoleAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 3-(6-methoxy-m-tolyl)-5-nitro-1,2-benzisothiazole (63.0 g, 0.210 mol), 5% acetic acid (1.52 L, 1.21 mol) and ethyl acetate (975 mL) is heated to 65° C., treated portionwise with iron powder (58.6 g, 1.05 mol), stirred at 65° C., and filtered through quartz filter paper. The filtrate phases are separated and the aqueous phase is extracted with ethyl acetate. The organic phase and extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product as an orange oil (55.7 g, 98.1%) which is identified by NMR spectral analyses.

Aufarbeitung

  1. filtrationfiltered through quartz
  2. filtrationfilter paper
  3. customThe filtrate phases are separated
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. washwashed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6600d888a400496c980450e7f345ea9e
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355796B1

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