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

HRID 735019ノート

反応式

HRID 735019 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

実験手順

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)).

後処理

  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

出典と根拠

ORDレコード
ord-f352719f350341d8a4c77dce60898658
出典データセット
uspto-grants-2009_09
特許番号
US07592373B2

反応ノート

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