Sulfuric Acid → HCID 86637890, compound

HRID 2389316Notes

Reaction equation

HRID 2389316 reaction equation
[C:1]([NH:4][C:5]1[C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=[CH:7][C:6]=1[NH:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(=O)[CH3:2].OS(O)(=O)=O.[OH-].[Na+]>CCO>[CH2:12]([O:11][C:10]1[C:5]2[N:4]=[C:1]([CH3:2])[N:19]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:6]=2[CH:7]=[CH:8][CH:9]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 68538779HCID 68538779, compound

Product 1

HCID 86637890HCID 86637890, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of ethyl N-[2-acetamido-3-(benzyloxy)phenyl]glycinate (2.82 g) in EtOH (28.2 mL) was added H2SO4 (1.62 g) at ambient temperature. The mixture was stirred at 70° C. for 1 hour. After cooling, the reaction mixture was added ice and alkalized with 2M NaOH aqueous solution (pH=8) under ice cooling. The formed precipitate was collected by filtration and washed with water to give ethyl [4-(benzyloxy)-2-methyl-1H-benzimidazol-1-yl]acetate (2.65 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was added ice
  3. filtrationThe formed precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-bfe25ec2338940d48c319f0f9bd09c29
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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