Phenyl isocyanate → N-benzyl-4-methyl-2-(3-phenylureido)thiazole-5-carboxamide

HRID 45369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45369
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.C(OCC)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:32]([NH:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:33])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Produkt 1

HCID 16897025N-benzyl-4-methyl-2-(3-phenylureido)thiazole-5-carboxamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-4-methylthiazole-5-carboxylic acid benzylamide (0.10 g, 0.40 mmol) in anhydrous tetrahydrofuran (5 mL), triethylamine (0.17 mL, 0.12 g, 1.22 mmol) and phenyl isocyanate (0.07 mL, 0.072 g, 0.61 mmol) were added dropwise at ambient temperature. The reaction mixture was stirred at ambient temperature for 25 h and then diluted with ethyl ether (20 mL). The white precipitate obtained was collected by filtration, washed with ethyl ether (3×6 mL) and dried under the reduced pressure to afford the title compound as a white solid in 80% yield (0.119 g); m.p.>300° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.00 (s, 1H), 8.47 (t, J=5.7 Hz, 1H), 7.46-7.17 (m, 10H), 7.03-6.98 (m, 1H), 4.35 (d, J=6.0 Hz, 2H), 2.43 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) δ 162.2, 140.2, 140.0, 129.4, 129.2, 128.7, 127.7, 127.1, 123.3, 119.1, 118.6, 43.0, 39.1; MS (ES+) m/z 367.2 (M+1).

Aufarbeitung

  1. customThe white precipitate obtained
  2. filtrationwas collected by filtration
  3. washwashed with ethyl ether (3×6 mL)
  4. customdried under the reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0366db3439354bc9903b6221769da6d2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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