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

HRID 1900127

反応式

HRID 1900127 の反応式
[H-].[Na+].[Cl:3][C:4]1[NH:5][C:6]2[C:12]([Cl:13])=[C:11]([Cl:14])[C:10]([Cl:15])=[C:9]([Cl:16])[C:7]=2[N:8]=1.[C:17]([O:20][CH2:21][CH2:22][O:23][CH2:24]Br)(=[O:19])[CH3:18]>CC#N>[Cl:3][C:4]1[N:5]([CH2:24][O:23][CH2:22][CH2:21][O:20][C:17](=[O:19])[CH3:18])[C:6]2[C:12]([Cl:13])=[C:11]([Cl:14])[C:10]([Cl:15])=[C:9]([Cl:16])[C:7]=2[N:8]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 3676562-(Bromomethoxy)ethyl acetateHCID 232739742,4,5,6,7-pentachloro-1H-benzimidazole

生成物 1

HCID 186975732,4,5,6,7-Pentachloro-1-(2-acetoxyethoxymethyl)benzimidazole

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

NaH (0.12 g, 3.0 mmole, 60% oil dispersion) 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.

後処理

  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

出典と根拠

ORDレコード
ord-b5d49d82bb8a4ef49d3eecc7828a6209
出典データセット
uspto-grants-1996_11
特許番号
US05574058

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