Sodium Iodide → HCID 22176584, 화합물

HRID 1797201노트

반응식

HRID 1797201 반응식
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[H-].[Na+].Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]#[N:30].[Na+].[I-]>CN(C=O)C.O>[OH:1][C:2]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])=[CH:16][CH:17]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrileHCID 22176571HCID 22176571, 화합물

생성물 1

HCID 22176584HCID 22176584, 화합물수율 107.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매3회

실험 절차

Into a 250 mL-3 neck flask fitted with a stirrer and thermometer, 400 mg of [2-hydroxy-2-(4-hydroxyphenyl)propyl][(methylethyl)sulfonyl]amine in DMF (10 mL) was added dropwise to 40 mg of NaH in DMF (30 mL) while stirring at room temperature under a nitrogen atmosphere. After stirring at this temperature for 30 minutes, 290 mg of alpha-bromo 2-cyanotoluene in DMF (10 mL) was added dropwise followed by the addition of 184 mg of NaI portion wise. The reaction was then heated at 100° C. for 2 hours. The mixture was cooled to room temperature and poured into H2O and the desired product was extracted with ethyl acetate. This organic layer was washed with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield 612 mg of a brown oil. This material was purified via silica gel chromatography employing the Chromatotron and using a 4000 micron rotor while eluting with a solvent of hexane/ethyl acetate 1:1 to yield intermediate title compound (161 mg, 28%) as a viscous oil. Ion spray M.S. 387.9 (M*−1).

후처리

  1. customInto a 250 mL-3 neck flask fitted with a stirrer
  2. stirringAfter stirring at this temperature for 30 minutes
  3. temperatureThe reaction was then heated at 100° C. for 2 hours
  4. temperatureThe mixture was cooled to room temperature
  5. extractionthe desired product was extracted with ethyl acetate
  6. washThis organic layer was washed with H2O
  7. dry with materialdried over K2CO3
  8. concentrationconcentrated under reduced vacuum

출처 및 근거

ORD 기록
ord-e189905c680c4f968025e5dbb699f5a0
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034045B1

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