Formic Acid → 2-(6-methoxy-1H-benzo[d]imidazol-1-yl)ethanol

HRID 624057Notes

Reaction equation

HRID 624057 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][CH2:11][CH2:12][OH:13].[CH:14](O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[CH:14][N:10]([CH2:11][CH2:12][OH:13])[C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 516892Sodium BicarbonateHCID 68830082N-(2-hydroxyethyl)-5-methoxy-2-aminoaniline

Product 1

HCID 450778812-(6-methoxy-1H-benzo[d]imidazol-1-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-((2-amino-5-methoxyphenyl)amino)ethanol (914 mg, 5.01 mmol) in THF (30 mL), formic acid (0.19 mL, 5.01 mmol) was added. After stirring at 80° C. for 30 min the reaction was allowed to reach rt and basified with conc. aq.NaHCO3-solution. The aq. layer was extracted with DCM (5×). The combined org. layers were dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield 2-(6-methoxy-1H-benzo[d]imidazol-1-yl)ethanol as a brown oil which was used as such in the next step. LC-MS conditions B: tR=0.30 min, [M+H]+=193.13.

Workup

  1. customto reach rt
  2. extractionThe aq. layer was extracted with DCM (5×)
  3. dry with materiallayers were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-15687ca6e1cd45c1890aea70a012b5d2
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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