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 surfed until H2 evolution has ceased and a clear solution was obtained (20 min.). (2-Acetoxyethoxy) methyl bromide (0.68 g, 10.68 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. Na2 SO4) 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, 2 H, C-1'), 4.143.92 (m, 4 H, C-3' and C-4'), 1.83 (s, 3 H, Ac). Anal. Calcd. for C12 H9N2Cl5O3 : 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. concentrationThe resulting mixture was concentrated under reduced pressure
3. additiondiluted with H2O (50 mL)
4. extractionextracted with EtOAc (100 mL)
5. washwashed with H2O (100 mL)
6. customdried (anhyd. Na2 SO4)
7. customthe solvent was removed under reduced pressure

ORDレコード

ord-6b209c5345d14b74892590b23cfe8f09

出典データセット

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05705490