Chlorotrimethylsilane → HCID 68005851, compound

HRID 74483Notes

Reaction equation

HRID 74483 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1.Cl[Si](C)(C)C.[O:17]1[CH2:21]CC[CH2:18]1.C[C:23](C)([O-:25])C.[K+]>COC(OC)OC>[CH3:18][O:17][CH:21]([O:25][CH3:23])[N:6]1[C:5]2[CH:10]=[CH:11][C:2]([I:1])=[CH:3][C:4]=2[N:8]=[C:7]1[CH3:9]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 178432243HCID 178432243, compound

Product 1

HCID 68005851HCID 68005851, compound

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture solution of 5-iodo-2-methyl-1H-benzimidazole (10 g, 39 mmol), trimethoxy-methane (200 ml), and chlorotrimethylsilane (0.075 ml, 0.59 mmol) was heated and stirred at 100° C. for five hours under a nitrogen atmosphere while distilling off the solvent (a reaction conversion rate of 97%). The reaction mixture was cooled to 40° C., and then a tetrahydrofuran solution (0.87 ml, 0.87 mmol) of potassium tert-butoxide was added thereto. This was concentrated under reduced pressure to provide crude 1-dimethoxymethyl-5-iodo-2-methyl-1H-benzimidazole.

Workup

  1. distillationwhile distilling off the solvent (a reaction conversion rate of 97%)
  2. temperatureThe reaction mixture was cooled to 40° C.
  3. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e69eb929755d4e1fa7d73d4c743ead21
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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