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Sodium Iodide → 4-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexyl iodide

HRID 1071632
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HRID 1071632 반응식
[C:1]([C:3]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[C:16]#[N:17])([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6]O)#[N:2].C(N(CC)CC)C.S(Cl)(C)(=O)=O.[I-:30].[Na+]>C(#N)C.[Cl-].[Na+].O.C(OCC)(=O)C>[C:1]([C:3]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[C:16]#[N:17])([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6][I:30])#[N:2]
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참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 223936344-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexanol

생성물 1

HCID 223938264-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexyl iodide수율 95.1%

시약·촉매·용매 3

HCID 6342
Acetonitrile
용매
HCID 8857Ethyl Acetate용매
HCID 57417360Sodium chloride; water용매

실험 절차

244 mg (0.98 mmol) of 4-cyano-5-methyl-4-(3-cyano-2-thienyl)hexanol was dissolved in 10 ml of acetonitrile and 0.16 ml (1.18 mmol) of triethylamine, and 83.6 μl (108 mmol) of mesyl chloride was added thereto. After about 5 minutes, 1.47 g (9.80 mmol) of sodium iodide was added. After completion of the reaction, brine and ethyl acetate were added, and the ethyl acetate layer was washed with an aqueous sodium thiosulfate aqueous solution and brine, dried over anhydrous magnesium sulfate and evaporated, to give a crude product. The crude product was subjected to silica gel (eluted at ethyl acetate:hexane=1:10), to give 334 mg (0.93 mmol, 95.1%) of the title compound as a yellow oil.

후처리

  1. additionwere added
  2. washthe ethyl acetate layer was washed with an aqueous sodium thiosulfate aqueous solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto give a crude product

출처 및 근거

ORD 기록
ord-b6ea499660b24c42b2a23b466c9f051e
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06906072B1

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