1-Bromopentane → HCID 19967445, 화합물

HRID 976629

반응식

HRID 976629 반응식
[H-].[Na+].[CH2:3]([O:10][NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][CH:16]=1)=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C)C=O.O>[CH2:3]([O:10][N:11]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:12]([NH:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:19][CH:20]=1)=[O:13])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 3

HCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 199673681-Benzyloxy-3-(4-butylphenyl)urea

생성물 1

HCID 19967445HCID 19967445, 화합물수율 62%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (0.14 g of 80% in mineral oil, 4.7 mmol) was added to a solution of 1-benzyloxy-3-(4-butylphenyl)urea (1.25 g, 4.2 mmol) in N,N-dimethylformamide (5 mL). The reaction mixture was heated briefly on a steam bath under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature then 1-bromopentane (0.63 g, 4.2 mmol) was added. The reaction mixture was heated at 90° C. overnight. The reaction mixture was cooled to ambient temperature, diluted with water and then extracted with diethyl ether. The organic layer was washed with water, dried with magnesium sulfate and then concentrated to provide 1.47 g of crude product as a brown oil. This material was purified by flash chromatography (silica gel; 1:19 ethyl acetate:hexanes) to provide 0.96 g of 1-benzyloxy-3-(4-butylphenyl)-1-pentylurea as an oil.

후처리

  1. temperatureThe reaction mixture was heated briefly on a steam bath under a nitrogen atmosphere
  2. temperatureThe reaction mixture was heated at 90° C. overnight
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customto provide 1.47 g of crude product as a brown oil
  9. customThis material was purified by flash chromatography (silica gel; 1:19 ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-161e249b100a4b4390ab9e5b292ca3c8
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05612377

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