Dimethylformamide → methyl 2-{4-[N-methyl-N-(2-benzimidazolyl)amino]phenoxy}propionate

HRID 1446873

反応式

HRID 1446873 の反応式
[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.Br[CH:20]([CH3:25])[C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:20]([CH3:25])[C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:13]=1)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 133148184-[N-methyl-N-(2-benzimidazolyl)amino]phenol

生成物 1

HCID 20553511methyl 2-{4-[N-methyl-N-(2-benzimidazolyl)amino]phenoxy}propionate収率 64.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-[N-methyl-N-(2-benzimidazolyl)amino]phenol (1.14 g), methyl 2-bromopropionate (0.80 g), anhydrous potassium carbonate (0.72 g) and dimethylformamide (25 ml) was heated for 4 hours at a temperature of 100° C. with vigorous stirring. After cooling, the mixture was poured into water and the aqueous solution was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by chromatography over silica gel with dichloromethane elution to give methyl 2-{4-[N-methyl-N-(2-benzimidazolyl)amino]phenoxy}propionate (1.0 g) as a colourless oil. The pmr spectrum of the compound was consistent with the assigned structure (CDCl3 ; chemical shift δppm): 1.50, d, 3H; 3.35, s, 3H; 3.70, s, 3H; 4.60, q, 1H; 6.50-7.60, m, 9H.

後処理

  1. temperatureAfter cooling
  2. extractionthe aqueous solution was extracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by chromatography over silica gel with dichloromethane elution

出典と根拠

ORDレコード
ord-1b968bdda4ef40b1a4f561ab5ca090bc
出典データセット
uspto-grants-1982_02
特許番号
US04314065

関連ノート

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