Oxalic Acid → N-(1-Methyl-3-pyrrolidinyl)-1-(phenylmethyl)-1H-benzimidazol-2-amine

HRID 1030507ノート

反応式

HRID 1030507 の反応式
[NH2:1][C:2]1[CH2:6][CH2:5][N:4]([CH3:7])[CH:3]=1.[CH2:8]([N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(=O)C(O)=O>C(O)C.CC(O)C>[CH3:7][N:4]1[CH2:5][CH2:6][CH:2]([NH:1][C:16]2[N:15]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=2)[CH2:3]1

参加物

5

反応物 3

HCID 971Oxalic AcidHCID 38219871-Benzyl-2-chlorobenzimidazoleHCID 198206613-amino-N-methyl pyrroline

生成物 1

HCID 9818015N-(1-Methyl-3-pyrrolidinyl)-1-(phenylmethyl)-1H-benzimidazol-2-amine

試薬・触媒・溶媒 1

HCID 22179027Isopropanol ethanol溶媒

反応条件

温度
125 °C

実験手順

To 14 g (0.14 mol) of 3-amino-N-methyl pyrroline was added 10.4 g (0.042 mol) of N-benzyl-2-chlorobenzimidazole and the reaction mixture heated to 125° C. for 2 days. The reaction mixture was partitioned between 150 mL of 1N NaOH and 100 mL of CH2Cl2. The aqueous layer was extracted again with 100 mL of CH2Cl2. The combined organic layers were washed with 100 mL of 1N NaOH, dried over Na2SO4, filtered, and concentrated by rotary evaporation and subjected to high vacuum at 100° C. for ~30 min. For purification, the residue was treated with 2 moles of oxalic acid in ethanol/2-propanol to afford 15 g (73%) of white analytically pure crystals, mp 211°-213° C. dec.

後処理

  1. customThe reaction mixture was partitioned between 150 mL of 1N NaOH and 100 mL of CH2Cl2
  2. extractionThe aqueous layer was extracted again with 100 mL of CH2Cl2
  3. washThe combined organic layers were washed with 100 mL of 1N NaOH
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. waitsubjected to high vacuum at 100° C. for ~30 min
  8. customFor purification
  9. customto afford 15 g (73%) of white analytically pure crystals, mp 211°-213° C. dec.

出典と根拠

ORDレコード
ord-7e7df78769fc4c87ba470923c231a5d9
出典データセット
uspto-grants-1992_04
特許番号
US05106857

反応ノート

読み込み中…