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

HRID 1900128노트

반응식

HRID 1900128 반응식
[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.[CH2:17]([O:24][CH2:25][CH2:26][O:27][CH2:28]Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[Cl:3][C:4]1[N:5]([CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[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

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 10998043BenzyloxyethoxymethylchlorideHCID 232739742,4,5,6,7-pentachloro-1H-benzimidazole

생성물 1

HCID 186975622,4,5,6,7-Pentachloro-1-(2-benzyloxyethoxymethyl)benzimidazole수율 38.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

NaH (0.033 g, 1.52 mmole, 90% oil dispersion) was added to a stirred suspension of 2,4,5,6,7-pentachlorobenzimidazole (14) (0.3 g, 1.03 mmole) in dry CH3CN (35 mL) under a N2 atmosphere. The solution was stirred until H2 evolution had ceased and a clear solution was obtained (20 min.). (2-Benzyloxyethoxy)methylchloride (0.31 g, 1.54 mmole) in CH3CN (10 mL) was then added dropwise. The reaction mixture was stirred for an additional 15 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. 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 followed by crystallization from hexane:EtOAc afforded 0.18 g (38.4%) of blocked product: m.p. 95° C.; 1H NMR (CDCl3): d 7.22-7.34 (m, 5H, C6H5), 5.93 (s, 2H, C-1'), 4.47 (s, 2H, CH2C6H5), 3.70-3.73 (m, 2H, C-3'), 3.45-3.57 (m, 2H, C-4'), 1.83 (s, 3H, Ac). Anal. Calcd. for C17H13NCl5O2 : C, 44.88; H, 2.86; N, 6.16. Found: C, 44.95; H, 2.59; N, 6.05.

후처리

  1. customa clear solution was obtained (20 min.)
  2. stirringThe reaction mixture was stirred for an additional 15 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
  9. customto yield an oil
  10. customThe resulting oil was purified by flash column chromatography (2×24 cm) (230-400 mesh)
  11. washElution of the column
  12. customwith hexane:EtOAc (6:4, v/v) and evaporation of the appropriate fractions
  13. customfollowed by crystallization from hexane

출처 및 근거

ORD 기록
ord-40f0cf5fb0704908950f77729d8755bf
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574058

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