Tetrahydrofuran → N-(3-Amino-4-thienyl)-N'-(2,6-dichlorophenyl)thiourea

HRID 349413

Reaktionsgleichung

Reaktionsgleichung von HRID 349413
Cl.Cl.[NH2:3][C:4]1[C:8]([NH2:9])=[CH:7][S:6][CH:5]=1.C1COCC1.C(N(C(C)C)C(C)C)C.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=1[N:32]=[C:33]=[S:34]>C(OCC)(=O)C>[NH2:3][C:4]1[C:8]([NH:9][C:33]([NH:32][C:26]2[C:27]([Cl:31])=[CH:28][CH:29]=[CH:30][C:25]=2[Cl:24])=[S:34])=[CH:7][S:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 127073423,4-Diaminothiophene dihydrochloride

Produkt 1

HCID 86037735N-(3-Amino-4-thienyl)-N'-(2,6-dichlorophenyl)thiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1.87 g of 3,4-diaminothiophene dihydrochloride, 60 ml of anhydrous THF and 2.58 g of N-ethyl-N,N-diisopropylamine was stirred at room temperature for 30 minutes and then admixed with 2.04 g of 2,6-dichlorophenyl isothiocyanate. After the mixture had been heated to 40° C. for 10 minutes, it was stirred at room temperature for approx. 18 hours, and the solvent was distilled off, and the residue admixed with water and extracted repeatedly with ethyl acetate. After the combined organic phases had been treated with activated carbon, they were dried over sodium sulfate and the solvent was again distilled off. A crystalline solid was obtained and, after stirring with a little ethyl acetate, was filtered off. M.p. 165° C.

Aufarbeitung

  1. temperatureAfter the mixture had been heated to 40° C. for 10 minutes
  2. stirringit was stirred at room temperature for approx. 18 hours
  3. distillationthe solvent was distilled off
  4. extractionthe residue admixed with water and extracted repeatedly with ethyl acetate
  5. additionAfter the combined organic phases had been treated with activated carbon, they
  6. dry with materialwere dried over sodium sulfate
  7. distillationthe solvent was again distilled off
  8. customA crystalline solid was obtained
  9. filtrationwas filtered off

Quellen und Nachweise

ORD-Eintrag
ord-241168cd9bac4a46b0fa26436f3bd4f8
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179830B2

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