Ethyl Acetate → N,4-dimethyl-1H-benzo[d]imidazole-2-carboxamide

HRID 1533749

反応式

HRID 1533749 の反応式
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[CH3:10][NH:11][C:12](=[O:18])[C:13](OCC)=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH3:9][C:3]1[C:2]2[N:1]=[C:13]([C:12](=[O:18])[NH:11][CH3:10])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 175932,3-DiaminotolueneHCID 516892Sodium BicarbonateHCID 3413434Ethyl 2-(methylamino)-2-oxoacetate

生成物 1

HCID 18355052N,4-dimethyl-1H-benzo[d]imidazole-2-carboxamide収率 37.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
175 °C

実験手順

A mixture of 2,3-diaminotoluene (2.0 g) and ethyl N-methyloxamate (2.36 g) in N,N-dimethylformamide (10 ml) was stirred at 175° C. for 8 hours. After being cooled to ambient temperature, the mixture was poured into a mixture of saturated aqueous sodium bicarbonate solution and ethyl acetate and the organic layer was separated. The organic layer was washed with brine and the solution was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (50:1) to give 4-methyl-2-(N-methylcarbamoyl)-1 H-benzimidazole (1.17 g) as a powder.

後処理

  1. temperatureAfter being cooled to ambient temperature
  2. customthe organic layer was separated
  3. washThe organic layer was washed with brine
  4. dry with materialthe solution was dried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (50:1)

出典と根拠

ORDレコード
ord-f9f8202b6033482b994e750c0abba420
出典データセット
uspto-grants-2001_03
特許番号
US06207693B1

関連ノート

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