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Water → diethyl 4-{[5-chloro-2-(N-methylcarbamoyl)phenyl]carbamoyl}benzylphosphonate

HRID 582236
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 582236
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].S(Cl)(Cl)=O.[CH3:23][NH:24][C:25]([C:27]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:28]=1[NH2:29])=[O:26].O>ClCCl.CN(C=O)C.N1C=CC=CC=1>[Cl:34][C:31]1[CH:32]=[CH:33][C:27]([C:25](=[O:26])[NH:24][CH3:23])=[C:28]([NH:29][C:14]([C:13]2[CH:12]=[CH:11][C:10]([CH2:9][P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:7][CH3:8])=[CH:18][CH:17]=2)=[O:16])[CH:30]=1
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Komponenten

8

Edukt 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 137458014-[(Diethoxyphosphoryl)methyl]benzoic acidHCID 138538282-Amino-4-chloro-N-methylbenzamide

Produkt 1

HCID 10961139diethyl 4-{[5-chloro-2-(N-methylcarbamoyl)phenyl]carbamoyl}benzylphosphonateAusbeute 53,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

27.2 g of 4-[(diethoxyphosphoryl)methyl]benzoic acid was suspended in a mixture of 60 ml of dichloromethane and 2 ml of DMF. 13.1 g of thionyl chloride was added, and the resulting mixture was refluxed for 1 hour. After completion of reaction, the reaction mixture was allowed to cool and then slowly added dropwise, with ice-cooling and stirring, to a solution of 18.5 g of 2-(N-methylcarbamoyl)-5-chloroaniline in a mixture of 50 ml of pyridine and 30 ml of dichloromethane. After completion of addition, the resulting mixture was stirred at room temperature for 48 hours. Then, 50 ml of water was added to the reaction mixture to precipitate crystals. The crystals were then collected by filtration, fully washed with water and dried, giving 23.6 g of diethyl 4-{[5-chloro-2-(N-methylcarbamoyl)phenyl]carbamoyl}benzylphosphonate.

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. customAfter completion of reaction
  3. temperatureto cool
  4. additionslowly added dropwise, with ice-
  5. temperaturecooling
  6. additionAfter completion of addition
  7. customto precipitate crystals
  8. filtrationThe crystals were then collected by filtration
  9. washfully washed with water
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5880536cc50242e5b33674dddea2597a
Quelldatensatz
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05922866

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