2-Aminothiazole → 1-(2-Cyclopentanesulfonyl-4-methyl-phenyl)-3-thiazol-2-yl-urea

HRID 131966

Reaktionsgleichung

Reaktionsgleichung von HRID 131966
[CH:1]1([SH:6])CCC[CH2:2]1.FC1C=C(C)C=CC=1[N+]([O-])=[O:15].[CH:18]1([S:23]([C:26]2[CH:27]=[C:28]([CH3:35])[CH:29]=[CH:30][C:31]=2[N+:32]([O-])=O)(=[O:25])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19]1.C1(S(C2C=C(C)C=CC=2N)(=O)=O)CCCC1.[NH2:52][C:53]1SC=[CH:56][N:57]=1>>[CH:18]1([S:23]([C:26]2[CH:27]=[C:28]([CH3:35])[CH:29]=[CH:30][C:31]=2[NH:32][C:56]([NH:57][C:53]2[S:6][CH:1]=[CH:2][N:52]=2)=[O:15])(=[O:25])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

6

Edukt 5

HCID 21552-AminothiazoleHCID 15510CyclopentanethiolHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 66998966HCID 66998966, Verbindung2×HCID 66998974HCID 66998974, Verbindung2×

Produkt 1

HCID 597327831-(2-Cyclopentanesulfonyl-4-methyl-phenyl)-3-thiazol-2-yl-ureaAusbeute 62 %

Versuchsvorschrift

3-Cyclopentanesulfanyl-4-nitrotoluene (0.83 g, 70%) was prepared from cyclopentyl mercaptan and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure A. This was oxidized to 3-cyclopentanesulfonyl-4-nitrotoluene (0.84 g, 90%) following general procedure R. 3-Cyclopentanesulfonyl-4-nitrotoluene was reduced to 2-cyclopentanesulfonyl-4-methyl-aniline (0.53 g, 70%) following general procedure C. 1-(2-Cyclopentanesulfonyl-4-methyl-phenyl)-3-thiazol-2-yl-urea (225 mg, 62%) was prepared from 2-cyclopentanesulfonyl-4-methyl-aniline (239 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Quellen und Nachweise

ORD-Eintrag
ord-a3b40849388c4b1abe1d6cc9acfc9eba
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384967B2

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