Sodium Iodide → HCID 66987547, compound

HRID 555274Notes

Reaction equation

HRID 555274 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:12][CH2:13][OH:14])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].[H-].[Na+].[CH3:19][S:20][CH2:21]Cl.[Na+].[I-]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].COCCOC.C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:12][CH2:13][O:14][CH2:19][S:20][CH3:21])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 66987301HCID 66987301, compound

Product 1

HCID 66987547HCID 66987547, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 1-(2-hydroxyethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (0.5 g. 2.27 mmol) in a mixture of dry THF:DME (25 mL:15 mL) was cooled to 5° C. NaH (0.081 g, 3.4 mmol) was added and stirred for 30 min at the same temperature. A mixture of chloromethyl methyl sulphide (0.285 g, 2.95 mmol) and NaI (0.408 g, 2.95 mmol) was then added slowly followed by TBAI (0.087 g, 0.22 mmol). The reaction was allowed to stir for overnight at ambient temperature. It was then quenched with saturated ammonium chloride solution and extracted with EtOAc. The organic layer was evaporated to give 0.53 g (83%) of 1-(2-methylsulfanylmethoxyethyl)-1H-benzimidazole-5-carboxylic acid methyl ester. 1H NMR (300 MHz, CDCl3) δ 1.9 (s, 3H), 3.9 (t, 2H), 3.95 (s, 3H), 4.4 (t, 2H), 4.6 (s, 2H), 7.45 (d, 1H), 8.05 (m, 2H), 8.5 (d, 1H)

Workup

  1. additionwas then added slowly
  2. stirringto stir for overnight at ambient temperature
  3. customIt was then quenched with saturated ammonium chloride solution
  4. extractionextracted with EtOAc
  5. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-c77c16136906438694f71f21c8229dd7
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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