Phosphorus oxychloride → HCID 20389616, compound

HRID 426672Notes

Reaction equation

HRID 426672 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH2:9][NH:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:18][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 53783902HCID 53783902, compound

Product 1

HCID 20389616HCID 20389616, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl [[2-(4-bromophenyl)-2-oxoethyl]amino]oxoacetate (35 g, 0.11 mole) and phosphorus oxychloride (150 ml) was maintained at reflux for 10.5 hours and cooled to room temperature. The solution was poured into a mixture of ice and water (3 liter) and stirred for 1.0 hour. The resulting solid was collected by filtration and air-dried. Recrystallization from methylcyclohexane gave 22.3 g (0.075 mole) of product (yield, 68%), m.p. 119.5°-122°.

Workup

  1. temperaturewas maintained
  2. temperatureat reflux for 10.5 hours
  3. filtrationThe resulting solid was collected by filtration
  4. customair-dried
  5. customRecrystallization from methylcyclohexane

Sources & evidence

ORD record
ord-d2237bfeaaa441579d9c87bd40c7f1c2
Source dataset
uspto-grants-1979_10
Patent number
US04171307

Reaction notes

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