Potassium Iodide → Methyl {2-[4-(3,5-difluorophenoxy)phenoxy]ethyl}carbamate

HRID 373786ノート

反応式

HRID 373786 の反応式
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:9][O:10][C:11](=[O:16])[NH:12][CH2:13][CH2:14]Cl.[F:17][C:18]1[CH:19]=[C:20]([CH:29]=[C:30]([F:32])[CH:31]=1)[O:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>CN(C)C=O>[CH3:9][O:10][C:11](=[O:16])[NH:12][CH2:13][CH2:14][O:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][C:20]2[CH:29]=[C:30]([F:32])[CH:31]=[C:18]([F:17])[CH:19]=2)=[CH:27][CH:26]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 251614Methyl (2-chloroethyl)carbamateHCID 133918364-(3,5-Difluorophenoxy)phenol

生成物 1

HCID 13502189Methyl {2-[4-(3,5-difluorophenoxy)phenoxy]ethyl}carbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

21.3 g of potassium carbonate powder, 1.5 g of finely powdered potassium iodide and 16 g of 2-chloroethylcarbamic acid methyl ester are added to a solution of 17.1 g of 4-(3,5-difluorophenoxy)-phenol in 100 ml of dimethylformamide, and the reaction mixture is heated at +95° C. for 15 hours. The reaction mixture is then cooled, poured onto ice-water and extracted repeatedly with ether. The combined ether phases are washed with water and dried over sodium sulfate. The solvent is distilled off completely. The crude product is purified further by chromatography over silica gel (eluant: petroleum ether (40° C.-65° C.)/diethyl ether, 5:1), yielding 2-[4-(3,5-difluorophenoxy)-phenoxy]-ethylcarbamic acid methyl ester, n21D : 1.5394.

後処理

  1. temperaturethe reaction mixture is heated at +95° C. for 15 hours
  2. temperatureThe reaction mixture is then cooled
  3. additionpoured onto ice-water
  4. extractionextracted repeatedly with ether
  5. washThe combined ether phases are washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent is distilled off completely
  8. customThe crude product is purified further by chromatography over silica gel (eluant: petroleum ether (40° C.-65° C.)/diethyl ether, 5:1)

出典と根拠

ORDレコード
ord-20e9f01896e3477e900d192ee018ec73
出典データセット
uspto-grants-1992_11
特許番号
US05166153

反応ノート

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