Phosphorus oxychloride → HCID 19921325, compound

HRID 1647870Notes

Reaction equation

HRID 1647870 reaction equation
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14].[C:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)#[N:17].P(Cl)(Cl)(Cl)=O>O>[C:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([N:2]([CH3:1])[C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=2[N+:13]([O-:15])=[O:14])=[O:23])=[CH:20][CH:19]=1)#[N:17]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 801724-Cyanobenzoyl chlorideHCID 7650848Methyl 4-(methylamino)-3-nitrobenzoate

Product 1

HCID 19921325HCID 19921325, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 13.1 g of methyl 4-methylamino-3-nitro-benzoate, 10.3 g of 4-cyano-benzoylchloride and 75 ml of phosphorusoxychloride is stirred for 8 hours at 100° C. After cooling, the mixture is decomposed with water and the aqueous phase is extracted with ethyl acetate. The ethyl acetate phases are washed with soda solution and concentrated by evaporation. The residue is dissolved in a little acetone and ether is slowly added. The quantities precipitated initially (about 1.2 g) are discarded. After further ether has been added the desired substance is precipitated. Yield: 10.2 g (48% of theory), Rf value: 0.54 (silica gel; ethyl acetate/petroleum ether =7:3)

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe ethyl acetate phases are washed with soda solution
  4. concentrationconcentrated by evaporation
  5. dissolutionThe residue is dissolved in a little acetone and ether
  6. additionis slowly added
  7. customThe quantities precipitated initially (about 1.2 g)
  8. additionAfter further ether has been added the desired substance
  9. customis precipitated

Sources & evidence

ORD record
ord-e4d196b5281f4014ada255254c5a7618
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

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