Phosphorus trichloride → HCID 86720867, compound

HRID 1398039Notes

Reaction equation

HRID 1398039 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH:10][C:11](=[O:13])[CH3:12].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)CC(OCC)=O)=[CH:17][CH:16]=1.P(Cl)(Cl)Cl>ClCCCl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[NH:10][C:11](=[O:13])[CH:12]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 101336Ethyl 3-(4-chlorophenyl)-3-oxopropanoateHCID 602062HCID 602062, compound

Product 1

HCID 86720867HCID 86720867, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of N′-(2-methoxyphenyl)acetohydrazide (2.90 g, 16.09 mmol) and ethyl 3-(4-chlorophenyl)-3-oxopropanoate (3.65 g, 16.09 mmol) in 10 mL of DCE was added drop wise phosphorus trichloride (1.41 mL, 16.09 mmol). The mixture was heated to 50° C. and all solids dissolved. After 2 hrs at 50° C. the mixture was cooled to RT and the ppt was collected by filtration and washed with water and EtOAc and dried to give 2.50 g (49%) of a white solid.

Workup

  1. dissolutionall solids dissolved
  2. temperatureAfter 2 hrs at 50° C. the mixture was cooled to RT
  3. filtrationthe ppt was collected by filtration
  4. washwashed with water and EtOAc
  5. customdried

Sources & evidence

ORD record
ord-ffde49dc0753402e9a404b6033cd3985
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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