Water → N-[5-bromo-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-N',N'-dimethylurea

HRID 4079

반응식

HRID 4079 반응식
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1.C(=O)(O)[O-].[Na+].[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27].O>C(Cl)(Cl)Cl>[Br:9][C:7]1[CH:6]=[CH:5][C:4]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)=[C:3]([NH:2][C:26]([N:25]([CH3:29])[CH3:24])=[O:27])[CH:8]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6598Dimethylcarbamoyl Chloride3회HCID 516892Sodium Bicarbonate3회HCID 138233211-(2-Amino-4-bromophenyl)indoline hydrochloride

생성물 1

HCID 13823369N-[5-bromo-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-N',N'-dimethylurea수율 40.3%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

To a stirred mixture, under nitrogen, of 28.9 g (0.10 mole) of 1-(2-amino-4-bromophenyl)indoline hydrochloride and 16.8 g (0.20 mole) of anhydrous powdered sodium bicarbonate in 500 ml of chloroform was added a solution of 21.5 g (0.20 mole) of dimethylcarbamyl chloride in 25 ml of chloroform, over a 10 minute period. The mixture was heated under reflux for 7 hours, and 8.4 g (0.10 mole) of sodium bicarbonate and 10.7 g (0.10 mole) of the dimethylcarbamyl chloride were added. After heating under reflux for 2 days, equivalent amounts (8.4 g of sodium bicarbonate and 10.7 g of dimethylcarbamyl chloride) were added. After three days under reflux, the mixture was cooled and 500 ml of water was added. The phases were stirred vigorously for 0.5 hours and separated. The organic phase was washed three times with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was dissolved in 200 ml of dichloromethane and adsorbed on a chromatography column containing 1 kg of silica gel packed in and eluted with dichloromethane. The fractions containing product were combined and concentrated to afford 14.5 g (40%) of product. Recrystallization from toluene (charcoal)/hexane gave the analytical sample, mp 119°-121° C.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 7 hours
  3. temperatureAfter heating
  4. temperatureunder reflux for 2 days
  5. temperatureAfter three days under reflux
  6. temperaturethe mixture was cooled
  7. customseparated
  8. washThe organic phase was washed three times with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. dissolutionThe residue was dissolved in 200 ml of dichloromethane
  12. additioncontaining 1 kg of silica gel
  13. washeluted with dichloromethane
  14. additionThe fractions containing product
  15. concentrationconcentrated

출처 및 근거

ORD 기록
ord-48a037212ff84f66a30fe0afce7b08b4
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723003

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