Methanol → HCID 178497374, compound

HRID 475171Notes

Reaction equation

HRID 475171 reaction equation
S(Cl)(Cl)=O.[NH:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:8]=2[N:7]=[CH:6]1.[CH3:17]O>>[NH:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:13][C:8]=2[N:7]=[CH:6]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178524171HCID 178524171, compound

Product 1

HCID 178497374HCID 178497374, compoundYield 90%

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (10 mL) was added dropwise to a solution of 1H-benzo[d]imidazole-5-carboxylic acid (4.8 g, 30 mmol) in MeOH (150 mL) cooled to 0° C. The reaction mixture was heated at reflux for 18 h, and then solvent (about 2/3) was concentrated under reduced pressure. After cooling, a yellow solid was precipitated from the solution and was filtered to afford 4 g (90%) of methyl 1H-benzo[d]imidazole-5-carboxylate (20): MS (ESI) m/z=177 [M+1]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationsolvent (about 2/3) was concentrated under reduced pressure
  4. temperatureAfter cooling
  5. customa yellow solid was precipitated from the solution
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-38edfee723044fc9a08700b16416d18b
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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