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

HRID 973418

반응식

HRID 973418 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매2회

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4825ff80ed504d4eac904674a4287a2c
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05063228

연결된 노트

불러오는 중…