Water → methyl 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoate

HRID 353815

反応式

HRID 353815 の反応式
[H-].[Na+].[N:3]1([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1.O>CN(C)C=O>[N:3]1([C:8]2[N:9]([CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=3)[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 69918962-(Pyrrolidin-1-yl)-1H-benzo[d]imidazole

生成物 1

HCID 12144533methyl 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (402 mg, 11 mmol) was added to a suspension of 2-pyrrolidino-1H-benzimidazole (1.9 g, 10.1 mmol) in dry N,N-dimethylformamide (30 mL). All solids dissolved. The solution was allowed to stir at ambient temperature for 15 minutes following the cessation of foaming. The solution was cooled to 5° C. and a solid formed. Methyl 4-(bromomethyl)benzoate (2.1 g, 01 mol) was added to the suspension and all the solids dissolved. The solution was allowed to stir at ambient temperature and a solid formed. The mixture was stirred at ambient temperature overnight and then it was poured into cold water. A solid was isolated by filtration, washed with water and dried to provide 3.0 g of crude product as an off-white solid. This material was recrystallized from methanol to provide methyl 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoate. Analysis: Calculated for C20H21N3O2: % C, 71.62; % H, 6.31; % N, 12.53. Found: % C, 71.44; % H, 6.41; % N, 12.50.

後処理

  1. dissolutionAll solids dissolved
  2. temperatureThe solution was cooled to 5° C.
  3. customa solid formed
  4. dissolutiondissolved
  5. stirringto stir at ambient temperature
  6. customa solid formed
  7. stirringThe mixture was stirred at ambient temperature overnight
  8. customA solid was isolated by filtration
  9. washwashed with water
  10. customdried
  11. customto provide 3.0 g of crude product as an off-white solid
  12. customThis material was recrystallized from methanol

出典と根拠

ORDレコード
ord-3f646bc23b97451a909f1edd272f55d1
出典データセット
uspto-grants-2004_06
特許番号
US06756382B2

関連ノート

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