Ammonia → HCID 22291402, 화합물

HRID 967812노트

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HRID 967812 반응식
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:13]([OH:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+].N>CN1CCN(C)C1=O>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:18]3[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][OH:21])=[CH:16][CH:17]=3)[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 17845791HCID 17845791, 화합물HCID 178418822HCID 178418822, 화합물

생성물 1

HCID 22291402HCID 22291402, 화합물수율 51%

시약·촉매·용매 1

HCID 66611,3-Dimethyl-2-imidazolidinone용매

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온도
180 °C

실험 절차

A mixture of 4-phenylimidazole (4.32 g, 30 mmol), Bromophenethyl alcohol (10.5 ml, 75 mmol), CuBr (10.4 g, 72 mmol) and Na2CO3 (3.8 g, 36 mmol) in 1,3-dimethyl-2-imidazolidinone (100 mL) was stirred at 180° C. for 36 h. After cooling, to the mixture was added 25% NH3 aq. (50 mL). After 30 min, insoluble materials were removed by Celite filtration and washed with dichloromethane. The aqueous layer was extracted with dichloromethane. The organic phase was dried (MgSO4) and concentrated under reduced pressure. To the residue was added diisopropylether (100 mL) and the flask was cooled to 0° C. Filtration of the diisopropylether gave 4.01 g of the title compound as colorless solid (51%): MS (ESI) m/z 265 [M+H]+, 1H-NMR (CDCl3) δ 2.94 (2H, t, J=6.4 Hz), 3.93 (2H, br), 7.26-7.30 (2H, m), 7.35-7.44 (5H, m), 7.55 (1H, d, J=1.2 Hz), 7.82-7.86 (3H, m).

후처리

  1. temperatureAfter cooling, to the mixture
  2. waitAfter 30 min
  3. custominsoluble materials were removed by Celite filtration
  4. washwashed with dichloromethane
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. additionTo the residue was added diisopropylether (100 mL)
  9. temperaturethe flask was cooled to 0° C
  10. filtrationFiltration of the diisopropylether

출처 및 근거

ORD 기록
ord-c4b662a8abe346eb959cb567c132e862
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956050B2

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