Water → 1-[4-(3-Chloropropoxy)-3-dimethylaminophenyl]ethanone

HRID 1533321노트

반응식

HRID 1533321 반응식
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[N:13]([CH3:15])[CH3:14].Br[CH2:17][CH2:18][CH2:19][Cl:20].O>CN(C)C=O>[Cl:20][CH2:19][CH2:18][CH2:17][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[N:13]([CH3:14])[CH3:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 12225608HCID 12225608, 화합물

생성물 1

HCID 101064281-[4-(3-Chloropropoxy)-3-dimethylaminophenyl]ethanone수율 179%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
3 °C

실험 절차

To a suspension of sodium hydride (2.3 g, 48.5 mmol of 50% oil dispersion) with dimethylformamide (75 ml), and cooled to 3° C. in an ice-salt bath and under a stream of nitrogen was added, dropwise, 1-(4-hydroxy-3-dimethylaminophenyl)ethanone (8.7 g, 48.5 mmol) dissolved in dimethylformamide (150 ml) so that The temperature did not go over 7° C. After the addition was over, the bath was removed and the reaction was stirred at ambient temperature for 45 minutes. The ice bath was reapplied and a solution of 1-bromo-3-chloropropane (8.4 g, 53.4 mmol) in dimethylformamide (25 ml) was added dropwise. After the addition was complete, the reaction was stirred for 18 hours at ambient temperature under nitrogen. The reaction was chilled to 7° C. in an ice bath and water (200 ml) was carefully added. After stirring for 5 minutes, the aqueous mixture was extracted with ethyl acetate (5×200 ml). The ethyl acetate extract was washed with water (2×50 ml), dried with MgSO4, and concentrated to yield 22.2 g of a black oily liquid. The compound was purified by prep HPLC, and combination of appropriate fractions gave 5.0 g of brown

후처리

  1. additionwas added
  2. customdid not go over 7° C
  3. additionAfter the addition
  4. customwas removed
  5. additionAfter the addition
  6. stirringthe reaction was stirred for 18 hours at ambient temperature under nitrogen
  7. temperatureThe reaction was chilled to 7° C. in an ice bath
  8. stirringAfter stirring for 5 minutes
  9. extractionthe aqueous mixture was extracted with ethyl acetate (5×200 ml)
  10. extractionThe ethyl acetate extract
  11. washwas washed with water (2×50 ml)
  12. dry with materialdried with MgSO4
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dbb8bdb962344abe84b732662cb20f23
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207680B1

반응 노트

불러오는 중…