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

HRID 636464ノート

反応式

HRID 636464 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3fcd7eac702f4abfb6a34465a205367f
出典データセット
uspto-grants-2001_02
特許番号
US06194396B1

反応ノート

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