Hydrochloric Acid → Methyl 4-aminothiophene-3-carboxylate

HRID 902507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902507
Cl.[CH3:2][O:3][C:4]([CH:6]1[C:10](=[N:11]O)[CH2:9][S:8][CH2:7]1)=[O:5]>CCOCC.CO>[CH3:2][O:3][C:4]([C:6]1[C:10]([NH2:11])=[CH:9][S:8][CH:7]=1)=[O:5]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 736752764-Hydroxyimino-tetrahydro-thiophene-3-carboxylic acid methyl ester

Produkt 1

HCID 2777610Methyl 4-aminothiophene-3-carboxylateAusbeute 111,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

HCl (1M solution in ether, 125 mL) was added slowly to a solution of 4-hydroxyimino-tetrahydro-thiophene-3-carboxylic acid methyl ester (34) (18.30 g, 104 mmol) in dry ether (200 mL) and dry methanol (50 mL) stirred at room temperature. The solution was further stirred at room temperature under argon for 24 h. The solids formed were filtered, washed by cold ether, and dried to yield 18.20 g (91%) of 4-amino-thiophene-3-carboxylic acid methyl ester as the hydrochloride salt. MP 198° C.; 1H NMR (400 MHz, DMSO-d6) δ 3.86 (s, 3H), 7.22 (d, J=2.4 Hz, 1H), 8.37 (d, J=3.2 Hz, 1H) ppm; MS m/z=158 amu (M++1).

Aufarbeitung

  1. stirringThe solution was further stirred at room temperature under argon for 24 h
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by cold ether
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4ad55c327e434144a0263f7b790a8d8c
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365200B2

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