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Hydrochloric Acid → N-[1-[4-(methylsulfonyl)phenyl]ethyl]ethane-1,2-diamine

HRID 420848
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HRID 420848 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH2:14]([NH2:17])[CH2:15][NH2:16].[BH4-].[Na+].Cl>CO.O1CCCC1>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:16][CH2:15][CH2:14][NH2:17])[CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 825294-MethylsulfonylacetophenoneHCID 4311764Sodium borohydride

생성물 1

HCID 60887768N-[1-[4-(methylsulfonyl)phenyl]ethyl]ethane-1,2-diamine수율 45.2%

시약·촉매·용매 2

HCID 887Methanol용매
2회
HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

4′-(Methylsulfonyl)acetophenone (1.0 g) and ethylenediamine (908 mg) were dissolved in methanol (10 ml), and the solution was heated at 50° C. for 3 hours. The reaction mixture was added with a suspension of sodium borohydride (286 mg) in tetrahydrofuran (50 ml), and then added with methanol (6 ml), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was made acidic with 1 N hydrochloric acid, and then the solvent was evaporated under reduced pressure. The mixture was added with distilled water and potassium carbonate and thereby neutralized, then the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1) to obtain the title compound (553 mg).

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe mixture was added with distilled water and potassium carbonate
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:0.1)

출처 및 근거

ORD 기록
ord-1cd4cfb811e545bca53f1fcec41f4c11
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08097708B2

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