3-Bromobenzyl bromide → 1-Bromo-3-[2,2-bis(ethoxycarbonyl)-2-(p-toluoylamino)ethyl]benzene

HRID 857221ノート

反応式

HRID 857221 の反応式
[O-]CC.[Na+].C(O)C.[C:8]1([CH3:28])[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:15])=[CH:10][CH:9]=1.[Br:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Br>C(O)C>[Br:29][C:30]1[CH:37]=[CH:36][CH:35]=[C:32]([CH2:33][C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:16][C:14]([C:11]2[CH:12]=[CH:13][C:8]([CH3:28])=[CH:9][CH:10]=2)=[O:15])[CH:31]=1

参加物

5

反応物 3

HCID 699793-Bromobenzyl bromideHCID 17447783Diethyl p-toluoylaminomalonateHCID 23706232Ethanol sodium ethoxide

生成物 1

HCID 218667981-Bromo-3-[2,2-bis(ethoxycarbonyl)-2-(p-toluoylamino)ethyl]benzene収率 107.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To 100 ml of dry ethanol, 21.45 g of 20% sodium ethoxide-ethanol solution and 17.61 g of diethyl p-toluoylaminomalonate were added and stirred for 30 minutes at room temperature under argon atmosphere. After 15.00 g of 3-bromobenzyl bromide was added dropwise, the reaction solution was stirred for 8 hours at 55° C. and then concentrated. To the residue was added water, and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to provide 29.82 g of the objective compound as yellow oil.

後処理

  1. stirringthe reaction solution was stirred for 8 hours at 55° C.
  2. concentrationconcentrated
  3. additionTo the residue was added water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-23ae2b5fcb95489c892ae4900b66172b
出典データセット
uspto-grants-2006_12
特許番号
US07144906B2

反応ノート

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