Diphenylamine → HCID 86634498、化合物

HRID 2080914ノート

反応式

HRID 2080914 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[CH:2].[C:12]1([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([N:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])#[CH:2]

参加物

4

反応物 2

HCID 11487DiphenylamineHCID 200388133-Ethynylbenzoyl chloride

生成物 1

HCID 86634498HCID 86634498、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of m-ethynylbenzoic acid and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50° C. for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride. To the m-ethynylbenzoyl chloride obtained was added a solution having 2.44 g (14.4 mmol) of diphenylamine dissolved in 7 ml of dichloromethane under ice-cooling and then the resultant mixture was stirred at room temperature for one hour. After completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water was added to the resultant residue. The mixture was extracted with 35 ml of ethyl acetate, the extract was dried over magnesium sulfate and the solvent was removed by distillation under reduced pressure using an evaporator. The resultant crude reaction product was purified by column chromatography (hexane/AcOEt10/1) using silica gel to obtain 0.7 g of 3-ethynyl-N,N-diphenylbenzamide which is a desired product as pale yellow liquid. (Yield: 35%)

後処理

  1. additionwas added a solution
  2. temperaturecooling
  3. customAfter completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water
  4. additionwas added to the resultant residue
  5. extractionThe mixture was extracted with 35 ml of ethyl acetate
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customan evaporator
  9. customThe resultant crude reaction product
  10. customwas purified by column chromatography (hexane/AcOEt10/1)

出典と根拠

ORDレコード
ord-90389f3c90e44679aad10908ef81f4fc
出典データセット
uspto-grants-2011_04
特許番号
US07932398B2

反応ノート

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