4-Bromoaniline → Pentanamide, N-(4-bromophenyl)-5-chloro-

HRID 840169

反応式

HRID 840169 の反応式
S(Cl)(Cl)=O.[Cl:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O.[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.ClCCl>[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][Cl:5])=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 78074-BromoanilineHCID 8471TriethylamineHCID 142445-Chlorovaleric acidHCID 24386Thionyl Chloride

生成物 1

HCID 532168Pentanamide, N-(4-bromophenyl)-5-chloro-

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

366 mmol (26.7 ml) of thionyl chloride are added dropwise to 183 mmol (25 g) of 5-chlorovaleric acid in 250 ml of toluene heated at reflux. The mixture is stirred at reflux until the evolution of gas has ceased and is then cooled. The solvent is evaporated off. The product obtained is then redissolved in 250 ml of dichloromethane and the temperature is lowered to 5° C. A solution of 183 mmol (31.5 g) of 4-bromoaniline in 100 ml of dichloromethane and 183 mmol (25.5 ml) of triethylamine are added in succession. The reaction mixture is stirred for 4 hours at 5° C. and then for 15 hours at room temperature. Hydrolysis, washing the organic phase with a 1N hydrochloric acid solution and evaporating off the solvents yields the expected product, which is used without being purified.

後処理

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureat reflux until the evolution of gas
  4. temperatureis then cooled
  5. customThe solvent is evaporated off
  6. customThe product obtained
  7. customis lowered to 5° C
  8. stirringThe reaction mixture is stirred for 4 hours at 5° C.
  9. customHydrolysis
  10. washwashing the organic phase with a 1N hydrochloric acid solution
  11. customevaporating off the solvents

出典と根拠

ORDレコード
ord-8ae5f806a52547179b454404a44bb294
出典データセット
uspto-grants-2002_04
特許番号
US06365605B1

関連ノート

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