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Diisopropylethylamine → 1-Amino-3-(4-carboxyphenyl)-2-thioxoimidazolidin-4-one

HRID 555626
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 555626
[N:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)=[C:2]=[S:3].C(N(C(C)C)CC)(C)C.Cl.[NH:23]([CH2:25][C:26](OCC)=[O:27])[NH2:24]>ClCCl>[NH2:24][N:23]1[CH2:25][C:26](=[O:27])[N:1]([C:4]2[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=2)[C:2]1=[S:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2429464-Isothiocyanatobenzoic acidHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Produkt 1

HCID 859639971-Amino-3-(4-carboxyphenyl)-2-thioxoimidazolidin-4-oneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

179 mg (1 mmol) of 4-isothiocyanatobenzoic acid and 523 μl (3 mmol) of diisopropylethylamine were stirred in 8 ml of dichloromethane and then with 155 mg (1 mmol) of ethyl hydrazinoacetate hydrochloride at room temperature for 96 hours. After the solvent was concentrated, the mixture was partitioned between ethyl acetate and 30% acetic acid. The aqueous layer was extracted with ethyl acetate again, and the organic layers were combined, washed with water and then with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated. The resulting solid was mixed with a 190:10:0.8 liquid mixture of ethyl acetate, methanol and acetic acid, and the insoluble was dried to obtain 132 mg of the desired product (yield 53%).

Aufarbeitung

  1. concentrationAfter the solvent was concentrated
  2. customthe mixture was partitioned between ethyl acetate and 30% acetic acid
  3. extractionThe aqueous layer was extracted with ethyl acetate again
  4. washwashed with water
  5. dry with materialwith saturated aqueous sodium chloride, dried over magnesium sulfate
  6. concentrationconcentrated
  7. additionThe resulting solid was mixed with a 190:10:0.8 liquid mixture of ethyl acetate, methanol and acetic acid
  8. customthe insoluble was dried

Quellen und Nachweise

ORD-Eintrag
ord-c629cad49e724fefb1e59aa5b27806bb
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08053453B2

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