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

HRID 1446873

반응식

HRID 1446873 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1b968bdda4ef40b1a4f561ab5ca090bc
출처 데이터셋
uspto-grants-1982_02
특허 번호
US04314065

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