Ammonia → HCID 22291402、化合物

HRID 967812ノート

反応式

HRID 967812 の反応式
[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

参加物

6

反応物 4

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 17845791HCID 17845791、化合物HCID 178418822HCID 178418822、化合物

生成物 1

HCID 22291402HCID 22291402、化合物収率 51%

試薬・触媒・溶媒 1

HCID 66611,3-Dimethyl-2-imidazolidinone溶媒

反応条件

温度
180 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c4b662a8abe346eb959cb567c132e862
出典データセット
uspto-grants-2005_10
特許番号
US06956050B2

反応ノート

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