O-Phenylenediamine → 2-(1-Methyl-3-pyrrolidinyl)-1H-benzimidazole

HRID 973418

反応式

HRID 973418 の反応式
[C:1]([CH:3]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4]1)#[N:2].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1N.[NH4+].[OH-]>Cl>[CH3:8][N:5]1[CH2:6][CH2:7][CH:3]([C:1]2[NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:2]=2)[CH2:4]1

参加物

5

反応物 3

HCID 7243O-PhenylenediamineHCID 14923Ammonium HydroxideHCID 108662851-Methylpyrrolidine-3-carbonitrile

生成物 1

HCID 199898622-(1-Methyl-3-pyrrolidinyl)-1H-benzimidazole

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒2 回

反応条件

温度
110 °C

実験手順

To 240 g of concentrated hydrochloric acid was added 43.2 g (0.39 mol) of 3-cyano-1-methylpyrrolidine (the temperature rose to 90° C.). After the temperature began to fall the solution was heated to 110° C. for 4 h. The solution was cooled to 60° C. and 42 g (0.39 mol) of 1,2-diaminobenzene in 250 mL of 1N hydrochloric acid was added. The solution was heated to reflux for 20 h. The cooled solution was made basic with concentrated NH4OH and the resulting crystals were collected by filtration. The product was chromatographed on a 7.5×36 cm silica column eluting with 1 gallon of 10% NH4OH-90% ethanol. The eluent was collected in 500-mL portions. The first 6 fractions were discarded and fractions 7-14 were collected and concentrated. The residue was recrystallized from ethyl acetate. Yield: 18 g (23%). A 5-g sample was recrystallized three times from ethyl acetate. Yield: 1.6 g, mp 189°-193° C.

後処理

  1. customrose to 90° C.
  2. temperatureThe solution was cooled to 60° C.
  3. temperatureThe solution was heated
  4. temperatureto reflux for 20 h
  5. filtrationthe resulting crystals were collected by filtration
  6. customThe product was chromatographed on a 7.5×36 cm silica column
  7. washeluting with 1 gallon of 10% NH4OH-90% ethanol
  8. customThe eluent was collected in 500-mL portions
  9. customfractions 7-14 were collected
  10. concentrationconcentrated
  11. customThe residue was recrystallized from ethyl acetate
  12. customA 5-g sample was recrystallized three times from ethyl acetate

出典と根拠

ORDレコード
ord-4825ff80ed504d4eac904674a4287a2c
出典データセット
uspto-grants-1991_11
特許番号
US05063228

関連ノート

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