Ethylene Oxide → Ethyl 5-(bis(2-hydroxyethyl)amino)-1-methyl-1H-benzimidazole-2-butanoate

HRID 514671ノート

反応式

HRID 514671 の反応式
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH3:17])[C:7]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:8][C:4]=2[CH:3]=1.[C:20]([O-:23])(=O)[CH3:21].[Na+].[CH2:25]1[O:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>O.CC(C)=O.ClCCl.C(O)(=O)C>[OH:27][CH2:26][CH2:25][N:1]([CH2:21][CH2:20][OH:23])[C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH3:17])[C:7]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:8][C:4]=2[CH:3]=1

参加物

9

反応物 4

HCID 6354Ethylene OxideHCID 11430Potassium CarbonateHCID 517045Sodium Acetate2 回HCID 29983307Ethyl 5-amino-1-methyl-1H-benzimidazole-2-butanoate2 回

生成物 1

HCID 13086945Ethyl 5-(bis(2-hydroxyethyl)amino)-1-methyl-1H-benzimidazole-2-butanoate収率 78.53%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 180Acetone溶媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
2.5 °C

実験手順

Ethyl 4-[5-amino-1-methyl-1H-benzimidazol-2-yl)butanoate (II, 200.0 g, 0.763 mol) was added to DM Water (1.1 L). Aqueous sodium acetate.3H2O (20.0 g sodium acetate.3H2O in 100 mL DM water) and acetic acid (400 mL) was added and agitated until complete dissolution of compound of the formula II. The reaction mixture was cooled to 0-5° C. and ethylene oxide (270.0 g, 6.12 mole) was added maintaining the temperature of the reaction mixture at 0-5° C. The reaction mixture was stirred at 0-5° C. for 5 hours. The temperature of reaction mixture was raised to 20-25° C. and agitated at 20-25° C. for 18 hours. After completion of the reaction, dichloromethane (2.0 L) was added at 20-25° C. followed by addition of aqueous solution of potassium carbonate (440.0 g potassium carbonate in 1.1 L DM water) portion wise at 20-25° C. to control the evaluation of effervescence and agitated at 20-25° C. for 5-10 minutes. The layers were separated. The organic layer (dichloromethane) was washed with DM water (1.0 L) twice and organic layer was concentrated under vacuum at 40-50° C. until a viscous mass was obtained. The viscous mass was dissolved in acetone (1.0 L), cooled to 0-5° C. and agitated at 0-5° C. for 1 hour. The solid separated out was filtered, washed with chilled (0-5° C.) acetone (200.0 mL) and dried at 40-50° C. under vacuum for 6 hours to give the title compound (III, 210.0 g; 78.53%), with a purity of 99.06%.

後処理

  1. temperaturemaintaining the temperature of the reaction mixture at 0-5° C
  2. customThe temperature of reaction mixture
  3. temperaturewas raised to 20-25° C.
  4. stirringagitated at 20-25° C. for 18 hours
  5. additionwas added at 20-25° C.
  6. stirringagitated at 20-25° C. for 5-10 minutes
  7. customThe layers were separated
  8. washThe organic layer (dichloromethane) was washed with DM water (1.0 L) twice
  9. concentrationorganic layer was concentrated under vacuum at 40-50° C. until a viscous mass
  10. customwas obtained
  11. temperaturecooled to 0-5° C.
  12. stirringagitated at 0-5° C. for 1 hour
  13. customThe solid separated out
  14. filtrationwas filtered
  15. washwashed
  16. temperaturewith chilled (0-5° C.) acetone (200.0 mL)
  17. customdried at 40-50° C. under vacuum for 6 hours

出典と根拠

ORDレコード
ord-93dd0e9dad7c4c53a87fbab6a3bc66c4
出典データセット
uspto-grants-2015_08
特許番号
US09108924B2

反応ノート

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