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

HRID 1030505ノート

反応式

HRID 1030505 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 2631-Butanol溶媒HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ea5da389261548618cadabe2b7e03535
出典データセット
uspto-grants-1992_04
特許番号
US05106857

反応ノート

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