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

HRID 1533749

반응식

HRID 1533749 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
175 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f9f8202b6033482b994e750c0abba420
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207693B1

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