Sodium hydride → 2,4,5,6,7-Pentachloro-1-(2-acetoxyethoxymethyl)benzimidazole

NaH (0.12 g, 3.0 mmole, 60% oil disperson) was added to a stirred suspension of 2,4,5,6,7-pentachlorobenzimidazole (14) (1.0 g, 3.4 mmole) in dry CH3CN (120 mL) under a N2 atmosphere. The solution was stirred until H2 evolution has ceased and a clear solution was obtained (20 min.). (2-Acetoxyethoxy) methyl bromide (0.68 g, 10.66 mmole) in CH3CN (34 mL) was then added dropwise. The reaction mixture was stirred for an additional 3 hr. The resulting mixture was concentrated under reduced pressure, diluted with H2O (50 mL), extracted with EtOAc (100 mL), washed with H2O (100 mL), dried (anhyd. Na2SO4) and the solvent was removed under reduced pressure to yield an oil (165). The resulting oil was purified by flash column chromatography (2×24 cm) (230-400 mesh). Elution of the column with hexane:EtOAc (6:4, v/v) and evaporation of the appropriate fractions gave a solid which was recrystallized from MeOH to afford 1.39 g (72%) of 165: m.p. 119° C. 1H NMR (CDCl3): d 5.93 (s, 2H, C-1'), 4.143.92 (m, 4H, C-3' and C-4'), 1.83 (s, 3H, Ac). Anal. Calcd. for C12H9N2Cl5O3 : C,35.45; H, 2.23; N, 6.89. Found: C, 35.57; H, 2.17; N, 16.91.

1. customa clear solution was obtained (20 min.)
2. stirringThe reaction mixture was stirred for an additional 3 hr
3. concentrationThe resulting mixture was concentrated under reduced pressure
4. additiondiluted with H2O (50 mL)
5. extractionextracted with EtOAc (100 mL)
6. washwashed with H2O (100 mL)
7. dry with materialdried (anhyd. Na2SO4)
8. customthe solvent was removed under reduced pressure

ORDレコード

ord-999f1fb3e4fe4b368a89d1f265e38c7e

出典データセット

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05646125