Reaktion #90404

ord-3fe1b9cfa3a94183ac5a08b02ce7cecf

Reaktionsgleichung

CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
VII
CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
(E)-N′-(2,7-dicyanobenzo[d]thiazol-6-yl)-N,N-dimethylformimidamide
Cc1ccc(N)cc1
4-toluidine
[Br-].[K+]
KBr
→
Cc1ccc(Nc2ncnc3ccc4nc(C#N)sc4c23)cc1
9-(p-Tolylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile
Ausbeute 64.0%

Edukte

CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
VII
CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
(E)-N′-(2,7-dicyanobenzo[d]thiazol-6-yl)-N,N-dimethylformimidamide
Cc1ccc(N)cc1
4-toluidine
[Br-].[K+]
KBr

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O.ClCCl
DCM EtOAc

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Prepared from VII and 4-toluidine. Flash chromatography eluent (DCM-EtOAc, 7:3). Yield: 64%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 3016, 2853, 2228, 1731, 1641, 1605, 1581, 1554, 1505, 1458, 1376, 1353, 1304, 1268, 1215, 1165, 1130, 976, 831, 811; 1H NMR (300 MHz, DMSO-d6) δ 8.49 (d, 1H, J=9.0 Hz), 8.07 (s, 1H), 7.76 (d, 1H, J=9.0 Hz), 7.20-7.17 (m, 2H), 7.12-7.05 (m, 2H), 2.32 (s, 3H); HRMS calcd for C17H12N5S (M+H+): 318.0813, found 318.0811.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09446044B2uspto-grants-2016_09