Hydrochloric Acid → 3-(3-Benzylureido)thiophene-2-carboxylic acid

HRID 576872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576872
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+].[CH2:19]([N:26]=[C:27]=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH2:19]([NH:26][C:27](=[O:28])[NH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 76639Benzyl isocyanateHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 533974903-(3-Benzylureido)thiophene-2-carboxylic acidAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of methyl 3-amino-thiophene-2-carboxylate 9.43 g (60 mmol) in acetonitrile 12 ml, 2N-sodium hydroxide 36 ml (72 mmol) was added and the mixture was stirred for 5 hrs. at 85° C. The reaction mixture was neutralized with 2N-hydrochloric acid 36 ml (72 mmol), then saturated sodium bicarbonate solution 50 ml and a solution of benzyl isocyanate 7.41 ml (60 mmol) in acetonitrile 36 ml were added and the mixture was stirred overnight. The reaction mixture was basified with 2N-sodium hydroxide 60 ml and washed with ether 100 ml. The aqueous phase was acidified with 2N-hydrochloric acid 85 ml. The aqueous phase was filtered and washed with H2O. The solid was dried in vacuo to obtain the title compound 6.46 g (yield 39%)

Aufarbeitung

  1. customat 85° C
  2. stirringthe mixture was stirred overnight
  3. washwashed with ether 100 ml
  4. filtrationThe aqueous phase was filtered
  5. washwashed with H2O
  6. customThe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1b9a9d3ea51d451991bfe0a067186dd9
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040531B2

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