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

HRID 840169

반응식

HRID 840169 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ae5f806a52547179b454404a44bb294
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365605B1

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