Acetic Acid → 1,2-dimethyl-4-methoxy-1H-benzimidazole

HRID 636464노트

반응식

HRID 636464 반응식
[NH2:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].[C:12](O)(=O)[CH3:13]>Cl>[CH3:5][N:4]1[C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH3:11])[C:2]=2[N:1]=[C:12]1[CH3:13]

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 106069363-methoxy-N1-methylbenzene-1,2-diamine

생성물 1

HCID 107024241,2-dimethyl-4-methoxy-1H-benzimidazole수율 87.5%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

A suspension of 2-amino-3-methoxy-N-methylaniline (671 mg) and acetic acid (265 mg) in 4N hydrochloric acid (3.5 ml) was refluxed for 10 hours. Insoluble material was filtered off, and the filtrate was adjusted to pH 7 with saturated sodium bicarbonate solution, and extracted with dichloromethane. The organic layers were combined, washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel flash chromatography (dichloromethane:methanol=40:1, v/v) to give 1,2-dimethyl-4-methoxy-lH-benzimidazole (680 mg). mp: 122.5-124° C.

후처리

  1. temperaturewas refluxed for 10 hours
  2. filtrationInsoluble material was filtered off
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel flash chromatography (dichloromethane

출처 및 근거

ORD 기록
ord-3fcd7eac702f4abfb6a34465a205367f
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194396B1

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