Methanamine, N-methoxy-, hydrochloride (1:1) → N-methoxy-N-methyl-1H-benzo[d]imidazole-4-carboxamide

HRID 1909005Notes

Reaction equation

HRID 1909005 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.Cl.[CH3:15][NH:16][O:17][CH3:18].C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH3:18][O:17][N:16]([CH3:15])[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 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 532310391H-benzoimidazole-4-carboxylic acid hydrochloride

Product 1

HCID 76845951N-methoxy-N-methyl-1H-benzo[d]imidazole-4-carboxamideYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1H-benzoimidazole-4-carboxylic acid hydrochloride (2.0 g, 10.1 mmol), N,O-dimethylhydroxylamine hydrochloride (1.47 g, 15.1 mmol) and ethyldiisopropylamine (7.02 mL, 40.3 mmol) in DMF (10 mL) at room temperature was added O-benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (3.90 g, 10.3 mmol) in a single portion. The mixture was stirred at room temperature overnight then concentrated in vacuo. Purification by SiO2 chromatography followed by trituration with EtOAc provided 1H-benzoimidazole-4-carboxylic acid methoxy-methyl-amide (945 mg).

Workup

  1. concentrationthen concentrated in vacuo
  2. customPurification by SiO2 chromatography

Sources & evidence

ORD record
ord-c2c79b29e3644f67967f261a280ebd87
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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