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

HRID 582236
Notes
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Reaction equation

HRID 582236 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

HCID 10961139diethyl 4-{[5-chloro-2-(N-methylcarbamoyl)phenyl]carbamoyl}benzylphosphonateYield 53.8%

Reagents, catalysts & solvents 3

HCID 1049
Pyridine
Solvent
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5880536cc50242e5b33674dddea2597a
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05922866

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes