Cesium carbonate → 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde

HRID 57429

反応式

HRID 57429 の反応式
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>[NH4+].[Cl-].[Cu]I.CN(C=O)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:1]2[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]2)=[CH:11][CH:10]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 125101-Chloro-4-iodobenzeneHCID 764281H-Imidazole-4-carbaldehydeHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

生成物 1

HCID 838830341-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde収率 107.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 1H-imidazole-4-carbaldehyde (3.71 g, 38.6 mmol), 1-chloro-4-iodobenzene (13.81 g, 57.9 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (1.10 g, 7.72 mmol), copper(I) iodide (0.368 g, 1.93 mmol) and cesium carbonate (25.2 g, 77 mmol) was added DMF (50 mL). The reaction was sealed and heated to 110° C. for 18 hours. The reaction mixture was then cooled to room temperature and diluted with a saturated solution of NH4Cl. A brown solid develops. Solid was collected, washed with water and air dried. Solid material was then dissolved in 10% MeOH:90% DCM solution and dried (Na2SO4), filtered and concentrated to afford a dark brown solid 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde (8.55 g, 41.4 mmol, 107% yield). Material as used without further purification. LCMS m/z 207.1 (M+H)+, Rt 0.58 min.

後処理

  1. customThe reaction was sealed
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customSolid was collected
  4. washwashed with water and air
  5. customdried
  6. dissolutionSolid material was then dissolved in 10% MeOH
  7. dry with material90% DCM solution and dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-3afaac30416d41f195407537c5aa6443
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

関連ノート

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