Dimethylformamide → HCID 178497376, compound

HRID 501806Notes

Reaction equation

HRID 501806 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.O1CCC[CH2:14]1.CN(C)C=O.C(Cl)(=O)C([Cl:26])=O>CO>[ClH:26].[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:14])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 178524171HCID 178524171, compound

Product 1

HCID 178497376HCID 178497376, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.00 g of 1H-benzimidazole-5-carboxylic acid was suspended in a mixed solvent of 10 mL of tetrahydrofuran and 20 μL of N,N-dimethylformamide, to which 1.6 mL of oxalyl chloride was added dropwise at room temperature, and this suspension was stirred for one hour at room temperature. The reaction mixture, to which 10 mL of methanol was added, was stirred for another one hour at room temperature and then for 30 minutes at 50° C., and this mixture was concentrated under reduced pressure. The resultant solid was washed with diisopropyl ether to yield 1.25 g of methyl 1H-benzimidazole-5-carboxylate hydrochloride as gray solid.

Workup

  1. additionwas added dropwise at room temperature
  2. stirringwas stirred for another one hour at room temperature
  3. waitfor 30 minutes at 50° C.
  4. concentrationthis mixture was concentrated under reduced pressure
  5. washThe resultant solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-8e13ecf182eb479887e5d740ef6c648b
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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