Dichloromethane → HCID 90241568, compound

HRID 1777123Notes

Reaction equation

HRID 1777123 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CN(C=O)C.O>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([O:11][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 124702491H-Benzimidazol-6-ol,1-methyl-(9CI)

Product 1

HCID 90241568HCID 90241568, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The mixture of 1-methyl-1H-benzo[d]imidazol-6-ol (600 mg, 4.03 mmol), BrCH2COOEt (372 mg, 4.03 mmol) and K2CO3 (1.1 g, 8.06 mmol) in DMF (8 mL) was stirred at room temperature for 16 h. DCM (100 mL) and water (100 mL) was then added to the reaction and the organic layer washed with water (50 mL), brine (50 mL) and dried over Na2SO4 before filtering and concentration to give the crude desired product (560 mg, Yield 60%). LCMS (m/z): 235.1 (M+1).

Workup

  1. washthe organic layer washed with water (50 mL), brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationbefore filtering
  4. concentrationconcentration

Sources & evidence

ORD record
ord-4faee4dcc81045ce96a47fe1a710ecff
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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