N-(2-Chlorophenyl)thiourea → HCID 86583826, Verbindung

HRID 2298643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2298643
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=1[CH3:10])=O.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]([NH2:25])=[S:24]>>[BrH:1].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]1[S:24][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=2[CH3:10])[N:25]=1

Komponenten

3

Edukt 2

HCID 737139N-(2-Chlorophenyl)thioureaHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Produkt 1

HCID 86583826HCID 86583826, VerbindungAusbeute 87,8 %

Versuchsvorschrift

Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (50 mg) was allowed to react with 2-chlorophenyl thiourea (26.7 mg) as described in Example 154, step (a), to give 58 mg (75%) of methyl 4-{2-[(2-chlorophenyl)amino]-(1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ2.66 (s, 3H), 3.82 (s, 3H), 7.04 (m, 1H), 7.32-7.38 (m, 2H), 7.47 (dd, 1H, J=1.4, 8.7 Hz), 8.12 (s, 1H), 8.56 (dd, 1H, J=1.4, 8.3 Hz), 9.75 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C16H13ClN2O2S3, 396.94 (M+H), found 397.1.

Quellen und Nachweise

ORD-Eintrag
ord-9847523de7ec464f81a609c0c307cb62
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06492403B1

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