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Water → 4-Benzyloxy-6-bromo-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole

HRID 969541
Notes
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Reaction equation

HRID 969541 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[NH:14][C:13]=2[CH:12]=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33].O>ClCCl>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:13]=2[CH:12]=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 672202147-(benzyloxy)-5-bromo-2-methyl-1H-benzo[d]imidazole

Product 1

HCID 462211624-Benzyloxy-6-bromo-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazoleYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18.6 g (58.6 mmol) 4-Benzyloxy-6-bromo-2-methyl-1H-benzimidazole and 9 ml (70.3 mmol) triethyl-amine were suspended in 370 ml dichloromethane and 13.9 ml (70.3 mmol) (2-chloromethoxy-ethyl)-trimethylsilane were added dropwise. The reaction was stirred at room temperature for 3 h, poured into water (400 ml) and extracted with dichloromethane (3×100 ml). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (toluene/dioxane=9:1) to afford 5.9 g (23%) of the title compound as a beige solid. m.p. 94°-95° C.

Workup

  1. extractionextracted with dichloromethane (3×100 ml)
  2. dry with materialThe organic layers were dried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (toluene/dioxane=9:1)

Sources & evidence

ORD record
ord-46f429a7d0034b62842b2b544695a356
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07307084B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes