Water → HCID 47159112, compound

HRID 1500839Notes

Reaction equation

HRID 1500839 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][OH:11].Cl[CH2:13][CH2:14][S:15]([CH3:18])(=[O:17])=[O:16].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:18][S:15]([CH2:14][CH2:13][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][OH:11])(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 785692-(Hydroxymethyl)-1H-benzimidazoleHCID 3035331-Chloro-2-methanesulfonylethane

Product 1

HCID 47159112HCID 47159112, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (1H-benzo[d]imidazol-2-yl)methanol (1.0 g, 6.75 mmol) and 1-chloro-2-(methylsulfonyl) ethane (1.05 g, 7.42 mmol) in DMF (3 mL) was stirred in the presence of K2CO3 (0.93 g, 6.75 mmol) at RT for overnight. The mixture was poured into water (20 mL) and extracted with DCM (50 mL×3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum to give the crude (1-(2-(methylsulfonyl)ethyl)-1H-benzo[d]imidazol-2-yl)methanol which was used for next step directly.

Workup

  1. extractionextracted with DCM (50 mL×3)
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aaf4b32d60624092969485c08fd0bbf3
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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