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

HRID 57429

반응식

HRID 57429 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3afaac30416d41f195407537c5aa6443
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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