Phosphorus oxychloride → HCID 21421764, compound

HRID 1730044Notes

Reaction equation

HRID 1730044 reaction equation
[C:1]1([CH:7]([N:9]2[C:13]([C:14]([NH2:16])=O)=[CH:12][N:11]=[CH:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]1([CH:7]([N:9]2[C:13]([C:14]#[N:16])=[CH:12][N:11]=[CH:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21421755HCID 21421755, compound

Product 1

HCID 21421764HCID 21421764, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred and cooled (-10° C.) solution of 3.7 parts of (-)-1-(1-phenylethyl)-1H-imidazole-5-carboxamide in 50 parts of pyridine are added dropwise, during a 15 minute period, 3.4 parts of phosphoryl chloride. The mixture is allowed to reach room temperature; then heated in a boiling water-bath for 1.5 hrs. The reaction mixture is cooled to room temperature and poured onto 250 parts of ice-water. The precipitated product is filtered off, washed with water and dissolved, in trichloromethane. The solution is dried, filtered and evaporated. The solid residue is crystallized from a mixture of 2,2'-oxybispropane and ethanol, yielding (-)-1-(1-phenylethyl)-1H-imidazole-5-carbonitrile; m.p. 128.7° C.; [α] = +40.23° (c = 1% CH3OH).

Workup

  1. additionare added dropwise, during a 15 minute period
  2. customto reach room temperature
  3. temperaturethen heated in a boiling water-bath for 1.5 hrs
  4. filtrationThe precipitated product is filtered off
  5. washwashed with water
  6. dissolutiondissolved, in trichloromethane
  7. customThe solution is dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe solid residue is crystallized from a mixture of 2,2'-oxybispropane and ethanol

Sources & evidence

ORD record
ord-eef581b05a0744ce88ae9c760ea4d4d8
Source dataset
uspto-grants-1976_11
Patent number
US03991072

Reaction notes

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