Phosphorus pentachloride → HCID 19976969, compound

HRID 1450523Notes

Reaction equation

HRID 1450523 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH:7]([C:10]1[CH:32]=[CH:31][C:13]([CH2:14][NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH3:9])[CH3:8].[N-:33]=[N+:34]=[N-:35].[Na+]>O>[C:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]2[N:15]([CH2:14][C:13]3[CH:31]=[CH:32][C:10]([CH:7]([CH3:9])[CH3:8])=[CH:11][CH:12]=3)[N:35]=[N:34][N:33]=2)=[CH:18][CH:19]=1)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 33557Sodium AzideHCID 19977082HCID 19977082, compound

Product 1

HCID 19976969HCID 19976969, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus pentachloride (0,249 g) was added to a solution of N-(4-isopropylbenzyl)-4-pivaloyloxybenzamide (0.353 g) in dichloeomethane (5 ml) under ice cooling, and stirring was continued for 2 h. This reaction mixture was added dropwise to a solution of sodium azide (0.78 g) in H2O (10 ml) at room temperature, and stirring was continued for 1 h. The mixture was extracted with chloroform, and the extract was washed with water, dried and evaporated to dryness. The residue was purified by column chromatography on silica gel with ethyl acetate-benzene (5/100) as an eluate and crystallization from hexane gave 0.2 g of the title compound.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. extractionThe mixture was extracted with chloroform
  4. washthe extract was washed with water
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on silica gel with ethyl acetate-benzene (5/100) as an eluate and
  8. customcrystallization from hexane

Sources & evidence

ORD record
ord-72056493d637446ea0ef7f73b3316150
Source dataset
uspto-grants-1997_02
Patent number
US05602161

Reaction notes

Loading…