Reaktion #90393

ord-381bd9c0e6b64cc483ef874fa4a4e7bd

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
Nc1ccc(O)cc1
4-aminophenol
[Br-].[K+]
KBr
→
N#Cc1nc2ccc3ncnc(Nc4ccc(O)cc4)c3c2s1
9-(4-Hydroxyphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile
Ausbeute 80.0%

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
Nc1ccc(O)cc1
4-aminophenol
[Br-].[K+]
KBr

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
EtOAc

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Prepared from VII and 4-aminophenol. Flash chromatography eluent (EtOAc). Yield: 80%; orange solid; mp 236° C.; IR (KBr) νmax/cm−1 3072, 2225, 1641, 1615, 1577, 1503, 1464, 1378, 1350, 1307, 1230, 1212, 1159, 1097, 972, 832; 1H NMR (300 MHz, DMSO-d6) δ 8.48 (d, 1H, J=8.7 Hz), 8.08 (m, 1H), 7.76 (d, 1H, J=8.7 Hz), 7.15 (m, 2H), 6.79 (m, 2H); HRMS calcd for C16H10N5OS (M+H+): 320.0606, found 320.0619.

Quelle

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