Dispersionsazofarbstoffe auf Aminobenzimidazolon-Basis

Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene

“…General Methods. All isolated new compounds were characterized on the basis of 1 H NMR and 13 C NMR spectroscopic data and HRMS data. 1 H NMR and 13 C NMR chemical shifts are reported in ppm using tetramethylsilane (TMS) as an internal standard.…”

“…(2-Oxo-2,3-dihydro-1H-benz[d]imidazol-1-yl)(phenyl)methyl acetate (6a): white solid; mp 165−166 °C; yield 79.1 mg (61%); 1 (5-Chloro-2-oxo-2,3-dihydro-1H-benz[d]imidazol-1-yl)(phenyl)methyl acetate (6v): white solid; mp 198−199 °C; yield 90.3 mg (62%); 1 H NMR (600 MHz, CDCl 3 ) δ 10.84 (s, 1H), 8.04 (s, 1H), 7.40−7.37 (m, 5H), 7.17 (d, J = 1.8 Hz, 1H), 6.88−6.86 (m, 1H), 6.72 (d, J = 8.4 Hz, 1H), 2.22 (s, 3H); 13 (5-Chloro-2-oxo- General Procedure for the Synthesis of Compound 10. Compound 6a (0.18 mmol, 1 equiv) was dissolved in 2-propanol (5 mL), and then concentrated hydrochloric acid (0.72 mmol, 4 equiv) was added.…”

“…1H-Benz[d]imidazol-2(3H)-one (10): 35 white solid; >312 °C; yield 18.3 mg (76%); 1 H NMR (400 MHz, DMSO-d 6 ) δ 10.56 (s, 2H), 6.90 (s, 4H); 13 C NMR (150 MHz, DMSO-d 6 ) δ 155.7, 130.1, 120.8, 108.9.…”

“…J = 1.8 Hz, 1H),6.92 (dd, J = 8.4, 1.8 Hz, 1H),6.71 (d, J = 8.4 Hz, 1H), 2.27 (s, 3H);13 C NMR (150 MHz, CDCl 3 ) δ 168.7, 154.7, 148.3, 141.6, 129.2, 128.5, 127.1, 125.4, 124.1, 121.8, 111.0, 110.9, 74.7, 20.6; HRMS (ESI) calcd for C 16 H 12 ClN 3 O 5 Na [M + Na] + 384.0358, found 384.0363. .97 (s, 1H), 7.37 (d, J = 9.0 Hz, 2H), 7.34 (d, J = 9.0 Hz, 2H), 7.16 (d, J = 2.4 Hz, 1H), 6.90 (dd, J = 8.4, 2.4 Hz, 1H), 6.71 (d, J = 8.4 Hz, 1H), 2.22 (s, 3H); 13 C NMR (150 MHz, CDCl 3 ) δ 168.8, 154.9, 135.1, 133.2, 129.3, 129.1, 128.2, 127.3, 125.7, 121.6, 111.3, 110.7, 75.1, 20.6; HRMS (ESI) calcd for C 16 H 12 Cl 2 N 2 O 3 Na [M + Na] + 373.0117, found 373.0125.…”

Physico–chemical and Dyeing Properties of Disperse Dyes containing Phthalimide Residues

“…Recently a series of patents and papers has been published on the use of similar compounds, containing heterocyclic amide systems, for the synthesis of disperse dyes. The use of pyridone-2 [31, benzimidazolone-2 [4], 1,3-quinazolone-4…”