Sodium Iodide → HCID 21744304, 화합물

HRID 483444노트

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HRID 483444 반응식
[CH3:1][N:2]([CH2:14][CH2:15][CH2:16][Cl:17])[C:3]([C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][N:6]=1)=[O:4].[F:18][C:19]1[CH:32]=[CH:31][C:22]([C:23]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN1CCCC1=O>[ClH:17].[ClH:17].[CH3:1][N:2]([CH2:14][CH2:15][CH2:16][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][N:25]1[C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([F:18])=[CH:32][CH:31]=1)[C:3]([C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][N:6]=1)=[O:4]

참가 물질

6

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HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2737266(4-Fluorophenyl)(piperidin-1-yl)methanoneHCID 19752303HCID 19752303, 화합물

생성물 1

HCID 21744304HCID 21744304, 화합물수율 9.4%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
120 °C

실험 절차

A mixture of N-methyl-N-(3-chloropropyl)-1,2-benzisothiazole-3-carboxamide (7.13 g), 1-(4-fluorobenzoyl)piperidine (6.44 g), potassium carbonate (7.33 g), and sodium iodide (300 mg) in dry 1-methyl-2-pyrrolidinone (150 ml) was heated to 120° C., with stirring, under nitrogen. After 24 hrs, the mixture was allowed to cool to room temperature, and the residue was partitioned between ethyl acetate/water. The organic phase was washed with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The crude residue was chromatographed twice on silica using 10:90 methanol:ethyl acetate as the eluent. The appropriate fractions were collected and evaporated. The residue was dissolved in ether and hydrogen chloride in ethanol was added. Recrystallized of the precipitate from dichloromethane/ether gave 0.642 g (5.09%) of product, mp 189°-191° C.

후처리

  1. temperatureto cool to room temperature
  2. customthe residue was partitioned between ethyl acetate/water
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude residue was chromatographed twice on silica using 10:90 methanol
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. dissolutionThe residue was dissolved in ether
  11. additionhydrogen chloride in ethanol was added
  12. customRecrystallized of the precipitate from dichloromethane/ether

출처 및 근거

ORD 기록
ord-cf2750056e904efd8a8552f159bcfc1c
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05225412

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