Fumaric Acid → 1-Ethyl-N-(1-methyl-3-pyrrolidinyl)-1H-benzimidazol-2-amine

HRID 1030505노트

반응식

HRID 1030505 반응식
Cl[C:2]1[N:6]([CH2:7][CH3:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N:3]=1.[NH2:13][CH:14]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15]1.C(O)(=O)/C=C/C(O)=O>C(O)CCC.C(O)(C)C.O>[CH2:7]([N:6]1[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[N:3]=[C:2]1[NH:13][CH:14]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15]1)[CH3:8]

참가 물질

7

반응물 3

HCID 444972Fumaric AcidHCID 37447962-chloro-1-ethyl-1H-1,3-benzodiazoleHCID 189403961-Methylpyrrolidin-3-amine

생성물 1

HCID 198206601-Ethyl-N-(1-methyl-3-pyrrolidinyl)-1H-benzimidazol-2-amine수율 63%

시약·촉매·용매 3

HCID 2631-Butanol용매HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

A solution of 38.6 g (0.21 mol) of 2-chloro-1-ethylbenzimidazole and 24 g (0.24 mol) of 3-amino-1-methylpyrrolidine in 150 mL of n-butanol was heated to reflux for 72 h and concentrated on the rotary evaporator (70° C./30 mm). The residue was partitioned between CHCl3 and dilute NaOH. The CHCl3 solution was dried (Na2SO4) and concentrated. For purification the material obtained was converted to the difumarate salt. The residue (68 g) was treated with a boiling solution of 64 g of fumaric acid in 600 mL of isopropyl alcohol and 100 mL of H2O. The resulting salt weighted 48 g (63% yield). A sample was recrystallized from ethanol-H2O, mp 204°-212° C. (dec).

후처리

  1. temperatureto reflux for 72 h
  2. concentrationconcentrated on the rotary evaporator (70° C./30 mm)
  3. customThe residue was partitioned between CHCl3 and dilute NaOH
  4. dry with materialThe CHCl3 solution was dried (Na2SO4)
  5. concentrationconcentrated
  6. customFor purification the material
  7. customobtained
  8. customA sample was recrystallized from ethanol-H2O, mp 204°-212° C. (dec)

출처 및 근거

ORD 기록
ord-ea5da389261548618cadabe2b7e03535
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05106857

반응 노트

불러오는 중…