Ammonia → tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate

HRID 735019노트

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HRID 735019 반응식
CNCCNC.Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]2([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[I-:25].[Na+].N>O1CCOCC1.[Cu]I>[C:20]([O:19][C:18](=[O:24])[NH:17][C:14]1([C:11]2[CH:12]=[CH:13][C:8]([I:25])=[CH:9][CH:10]=2)[CH2:16][CH2:15]1)([CH3:23])([CH3:22])[CH3:21]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 53216208tert-Butyl (1-(4-bromophenyl)cyclopropyl)carbamate

생성물 1

HCID 59019959tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

실험 절차

0.43 mL (4 mmol) of N,N′-dimethylethylenediamine is added to a reaction mixture of 0.4 g (2 mmol) of copper (I) iodide, 6.2 g (19.86 mmol) of tert-butyl [1-(4-bromophenyl)-cyclopropyl]carbamate, and 6 g (40 mmol) of sodium iodide in 15 mL of 1,4-dioxane and refluxed for 24 hours under nitrogen. Then the cooled suspension is combined with 30% ammonia solution, poured onto distilled water, and extracted with dichloromethane. The organic phase is dried over sodium sulfate, filtered, and the solvent is distilled off. Yield: 6.60 g (93% of theory); C14H18INO2 (M=359.20); calc.: molecular ion peak (M+H)+: 360; found: molecular ion peak (M+H)+: 360; Rf value: 0.8 (silica gel, dichloromethane/ethanol (50:1)).

후처리

  1. temperaturerefluxed for 24 hours under nitrogen
  2. additionpoured
  3. distillationonto distilled water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. distillationthe solvent is distilled off

출처 및 근거

ORD 기록
ord-f352719f350341d8a4c77dce60898658
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592373B2

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