2-Benzyl-1,2,5-thiadiazolidine 1,1-dioxide → N-benzyl-2-(5-benzyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide

HRID 560796

Reaktionsgleichung

Reaktionsgleichung von HRID 560796
C(N1CCNC1=NC#N)C1C=CC=CC=1.[CH2:16]([N:23]1[CH2:27][CH2:26][NH:25][S:24]1(=[O:29])=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:30]([NH:37][C:38]([C:40]1[S:44][C:43](Br)=[N:42][C:41]=1[CH3:46])=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:30]([NH:37][C:38]([C:40]1[S:44][C:43]([N:25]2[CH2:26][CH2:27][N:23]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:24]2(=[O:29])=[O:28])=[N:42][C:41]=1[CH3:46])=[O:39])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Komponenten

4

Edukt 3

HCID 103758902-Benzyl-1,2,5-thiadiazolidine 1,1-dioxideHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamideHCID 178512076HCID 178512076, Verbindung

Produkt 1

HCID 59481243N-benzyl-2-(5-benzyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-methyl-1,3-thiazole-5-carboxamideAusbeute 78 %

Versuchsvorschrift

Following the procedure as described in Example 27, making variations as required to replace N-(1-benzylimidazolidin-2-ylidene)cyanamide with 2-benzyl-1,2,5-thiadiazolidine 1,1-dioxide to react with N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 78% yield: mp 135-137° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.37-7.26 (m, 10H), 5.99 (t, J=5.6 Hz, 1H), 4.55 (d, J=5.6 Hz, 2H), 4.25 (s, 2H), 4.00 (t, J=6.6 Hz, 2H), 3.39 (t, J=6.6 Hz, 2H), 2.57 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.5, 156.6, 153.4, 137.7, 133.7, 128.9, 128.8, 128.6, 127.8, 127.7, 119.4, 51.4, 45.0, 44.1, 43.9, 17.3; MS (ES+) m/z 443.2 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-43881f937dc14defbc7d96aa7614d370
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063084B2

Verknüpfte Notizen

Wird geladen…