Potassium Carbonate → Methyl 3-amino-6-nitro-1-benzothiophene-2-carboxylate

HRID 235061

Reaktionsgleichung

Reaktionsgleichung von HRID 235061
[N+]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[C:15]([O:19][CH2:20]C)(=[O:18])[CH2:16][SH:17].C([O-])([O-])=O.[K+].[K+]>C(O)C>[NH2:7][C:6]1[C:5]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:4]=2[S:17][C:16]=1[C:15]([O:19][CH3:20])=[O:18]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 5540822,4-Dinitrobenzonitrile

Produkt 1

HCID 619888Methyl 3-amino-6-nitro-1-benzothiophene-2-carboxylateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The product from Example 47B (3.73 g, 19.3 mmol) was treated with 1 equivalent ethyl thioglycolate and 1 equivalent K2CO3 in ethanol by the procedure described in Example 41A to yield the title compound (2.35 g, 46%). m.p. 169°-170° C. 1H NMR (300 MHz, DMSO) δ8.90 (d, 1H), 8.37 (d, 1H), 8.20 (dd, 1H), 7.29 (br s, 2H), 4.31 (q, 2H), 1.31 (t, 3H). MS (DCI/NH3) m/e 284 (M+NH4)+.

Quellen und Nachweise

ORD-Eintrag
ord-d04c0d47fae94a77b33d7e29cc02dd36
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597823

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