Water → 2-Chloro-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole

HRID 912886Notes

Reaction equation

HRID 912886 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:4]=2[N:3]=1.C(N(CC)CC)C.Cl[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28].O>ClCCl>[Cl:1][C:2]1[N:6]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:5]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178506089HCID 178506089, compound

Product 1

HCID 674013802-Chloro-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-5-trifluoromethyl-1H-benzoimidazole (1 g, 4.52 mmol, Example 1c), triethylamine (1.3 mL, 9.04 mmol, Aldrich) and (2-chloromethoxy-ethyl)-trimethyl-silane (881 μL, 4.98 mmol, Aldrich) in dichloromethane (30 mL) was stirred at room temperature for 16 h. Water (150 mL) was added, and the mixture was extracted with dichloromethane (2×150 mL). The combined organic extracts were dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with hexane/EtOAc (10:1) to give the title compound as an orange solid. MS (ESI, positive ion) m/z: 351 (M+1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×150 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with hexane/EtOAc (10:1)

Sources & evidence

ORD record
ord-42298533561540f29d2ed4c8d8b83c08
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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