Water → 2-[(1-methyl-1H-1,3-benzodiazol-5-yl)oxy]acetic acid

HRID 1429461Notes

Reaction equation

HRID 1429461 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([OH:13])=[CH:12][C:7]=2[N:6]=[CH:5]1.Br[CH2:15][C:16]([O:18]CC)=[O:17].O>CN(C=O)C>[CH3:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([O:13][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][C:7]=2[N:6]=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 8404451-Methyl-1H-benzo[d]imidazol-5-ol

Product 1

HCID 846739552-[(1-methyl-1H-1,3-benzodiazol-5-yl)oxy]acetic acidYield 27.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (204 mg, 8.49 mmol) in DMF (5 mL) was added 1-methyl-1H-benzo[d]imidazol-5-ol (420 mg, 2.83 mmol) at 28° C. After being stirred for 5 minutes, ethyl 2-bromoacetate (568 mg, 3.4 mmol) was added and the resulting mixture stirred for a further 16 h under the reaction was complete by TLC. The mixture was treated with water (50 mL) and extracted with ethyl acetate (2×20 mL). The water layer was treated with 2N HCl until pH 3 and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the product (160 mg, 24.1%) as white solid which was used in next step without further purification. LCMS (m/z): 207.1 (M+1).

Workup

  1. stirringthe resulting mixture stirred for a further 16 h under the reaction
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. additionThe water layer was treated with 2N HCl until pH 3
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8b50b23945844dc6a02833cc63dba04b
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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