Benzocaine → Ethyl 4-{[3-(4-chlorophenyl)propyl]amino}benzoate

HRID 2052519

Reaktionsgleichung

Reaktionsgleichung von HRID 2052519
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.S(O[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)(=O)(=O)C.CN(C)P(N(C)C)(N(C)C)=O.O1CCCC1>O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][CH2:18][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 2337BenzocaineHCID 8028TetrahydrofuranHCID 12679HexamethylphosphoramideHCID 13079705HCID 13079705, Verbindung

Produkt 1

HCID 13079692Ethyl 4-{[3-(4-chlorophenyl)propyl]amino}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 49.5 g. of ethyl 4-aminobenzoate, 34.9 g. of 3-(p-chlorophenyl)propanol O-mesylate in 100 ml. of hexamethylphosphoramide is heated at 125°-130° C. for 16 hours. The solution is diluted with 50 ml. of tetrahydrofuran and with 150 ml. of water. Chilling and filtering gives crystals which are washed with water and recrystallized from ethanol to give 28.3 g. of light yellow crystals. Recrystallizations give the product as crystals, m.p. 122°-124° C.

Aufarbeitung

  1. additionThe solution is diluted with 50 ml
  2. temperatureChilling
  3. filtrationfiltering
  4. customgives crystals which
  5. washare washed with water
  6. customrecrystallized from ethanol
  7. customto give 28.3 g
  8. customRecrystallizations

Quellen und Nachweise

ORD-Eintrag
ord-393350e9c5234997b8aa07446456191c
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04185115

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