Phenol → 3-(4-chlorophenoxy)-N-[3-(imidazol-1-yl)propyl]propionamide

HRID 1956834

반응식

HRID 1956834 반응식
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.ClC1C=CC(O)=CC=1.C1(O)C=CC=CC=1.O(CCC(O)=O)C1C=CC=CC=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:53][CH2:54][CH2:55][CH2:56][N:57]1[CH:61]=[CH:60][N:59]=[CH:58]1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][C:9]([NH:53][CH2:54][CH2:55][CH2:56][N:57]2[CH:61]=[CH:60][N:59]=[CH:58]2)=[O:11])=[CH:12][CH:13]=1

참가 물질

8

반응물 6

HCID 996PhenolHCID 46844-ChlorophenolHCID 682631,1'-CarbonyldiimidazoleHCID 767803-(4-Chlorophenoxy)propionic acidHCID 787361H-Imidazole-1-propanamineHCID 815963-Phenoxypropionic acid

생성물 1

HCID 183498083-(4-chlorophenoxy)-N-[3-(imidazol-1-yl)propyl]propionamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-(4-chlorophenoxy)propionic acid (5.0 g, prepared from 4-chlorophenol by the process described in J.A.C.S. 1923, 2708 for the conversion of phenol into 3-phenoxypropionic acid) in THF (90 ml) was treated with 1,1'-carbonyldiimidazole (4.05 g) at room temperature with stirring. The mixture was stirred at ambient temperature for two hours. 1-(3-Aminopropyl)imidazole (3.12 g) was added and the mixture was stirred at ambient temperature for 18 hours. The solvent was distilled off and the residue was dissolved in dichloromethane, washed with water, dried and then evaporated to give a solid which was recrystallised from ethyl acetate to give 3-(4-chlorophenoxy)-N-[3-(imidazol-1-yl)propyl]propionamide, m.p. 114°-115.5° C.

후처리

  1. stirringThe mixture was stirred at ambient temperature for two hours
  2. stirringthe mixture was stirred at ambient temperature for 18 hours
  3. distillationThe solvent was distilled off
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customto give a solid which
  9. customwas recrystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-12330c4a033a4ed0a914490f75aff133
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05780642

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