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Ammonium Chloride → HCID 67181910, 화합물

HRID 2425552
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HRID 2425552 반응식
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1/[CH:8]=[N:9]/[S@@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11].[CH3:16][Mg]Br.[Cl-].[NH4+]>ClCCl>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C@@H:8]([NH:9][S@@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[CH3:16]
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참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 87300875HCID 87300875, 화합물HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 67181910HCID 67181910, 화합물수율 53.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

(R,E)-N-((5-chloro-1-methyl-1H-pyrazol-4-yl)methylene)-2-methylpropane-2-sulfinamide (100 mg, 0.404 mmol) was dissolved in dichloromethane (10 ml) placed under nitrogen and cooled to −78° C. 1.4M methyl magnesium bromide solution (toluene:THF 3:1, 1.04 ml, 1.45 mmol) was added dropwise and reaction stirred overnight while warming to room temperature. Saturated aqueous ammonium chloride solution (20 ml) was added to the reaction and stirred for 5 minutes. The product was extracted with EtOAc (2×15 ml), combined organics were washed with brine (15 ml), dried over Na2SO4, filtered and concentrated and purified by silica gel column chromatography eluted with heptane/ethyl acetate=100/0 to 0/100 to furnish the title product as a clear gum (57 mg, 53% yield). 1H NMR (400 MHz, CD3OD) 1.18-1.19 (9H s) 1.54-1.56 (3H d) 3.81-3.82 (3H s) 4.41-4.47 (1H q) 7.50-7.51 (1H s) MS (ESI) m/z 264 (M+H)+

후처리

  1. customreaction
  2. temperaturewhile warming to room temperature
  3. stirringstirred for 5 minutes
  4. extractionThe product was extracted with EtOAc (2×15 ml)
  5. washcombined organics were washed with brine (15 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography
  10. washeluted with heptane/ethyl acetate=100/0 to 0/100

출처 및 근거

ORD 기록
ord-51589c0e9360402086496564f04a268e
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07964732B2

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