Dimethylformamide → tert.-Butyl (3-chloropropyl)-[2-(4-cyanophenyl)ethyl]carbamate

HRID 1591757노트

반응식

HRID 1591757 반응식
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:7][CH:6]=1)#[N:4].CN(C)C=O.Br[CH2:27][CH2:28][CH2:29][Cl:30]>O1CCCC1>[Cl:30][CH2:29][CH2:28][CH2:27][N:13]([CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=1)[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 21955533tert-Butyl 4-cyanophenethylcarbamate

생성물 1

HCID 58638721tert.-Butyl (3-chloropropyl)-[2-(4-cyanophenyl)ethyl]carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

At room temperature, 0.23 g (9.03 mmol) of sodium hydride (95%) was added to a solution of 1.482 g (6.02 mmol) of tert.-butyl [2-(4-cyanophenyl)ethyl]carbamate in 25 ml of tetrahydrofuran/25 ml of dimethylformamide. The mixture was stirred for a further 15 minutes. 1.49 ml (15.04 mmol) of 1-bromo-3-chloropropane were then added, and the reaction mixture was stirred at room temperature overnight. With ice bath cooling, the mixture was then quenched with water, and extracted with ethyl acetate. The organic extracts were washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The crude product obtained in this manner was purified by column chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 4:1).

후처리

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. temperatureWith ice bath cooling
  3. customthe mixture was then quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-adc6e36eafb94085ac6bf8a246d1351a
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291642B2

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