Dimethylamine → 1H-benzoimidazole-4-carboxylic acid dimethylamide

HRID 1909003Notes

Reaction equation

HRID 1909003 reaction equation
Cl.[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([OH:13])=O)[C:5]=2[N:4]=[CH:3]1.[CH3:14][NH:15][CH3:16].C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH3:14][N:15]([CH3:16])[C:11]([C:10]1[C:5]2[N:4]=[CH:3][NH:2][C:6]=2[CH:7]=[CH:8][CH:9]=1)=[O:13]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 532310391H-benzoimidazole-4-carboxylic acid hydrochloride

Product 1

HCID 672867491H-benzoimidazole-4-carboxylic acid dimethylamideYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1H-benzoimidazole-4-carboxylic acid hydrochloride (1 g, 5.04 mmol), dimethylamine (2M in THF; 3.78 mL, 7.55 mmol) and ethyldiisopropylamine (3.51 mL, 20.1 mmol) in DMF (5.0 mL) at room temperature was added O-benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (1.95 g, 5.14 mmol) in a single portion. The mixture was stirred at room temperature overnight then concentrated in vacuo. The product was purified by SiO2 chromatography followed by trituration with Et2O providing 1H-benzoimidazole-4-carboxylic acid dimethylamide (730 mg).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe product was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-5077414802ed49d5b118970a09aaba9e
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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