Phosphorus pentachloride → HCID 68296440, compound

HRID 631885Notes

Reaction equation

HRID 631885 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:7]([NH:14][C:15](=O)[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:25])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:27]([Si](C)(C)C)=[N+:28]=[N-:29].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH2:7]([N:14]1[C:15]([C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:25])=[N:29][N:28]=[N:27]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 78378AzidotrimethylsilaneHCID 516892Sodium BicarbonateHCID 19805433N-benzyl-2-methyl-6-nitrobenzamide2×

Product 1

HCID 68296440HCID 68296440, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Phosphorous pentachloride (0.42 g, 2 mmol) was added to a solution of N-benzyl-2-methyl-6-nitrobenzamide (Intermediate 19, 0.54 g) in DCM (10 mL). The mixture was stirred under nitrogen for 30 minutes and then azidotrimethylsilane (0.48 g) was added and the mixture was stirred for a further 72 hours. The mixture was diluted with DCM (50 mL) and water (50 mL). Solid sodium bicarbonate was then added to the mixture until there was no further gaseous evolution. The organic solution was washed with saturated aqueous sodium bicarbonate, then with 1N hydrochloric acid, dried with magnesium sulfate and filtered. The solvent was evaporated to give an orange solid which was recrystallised from ethyl acetate to give the title compound as a white solid (0.42 g).

Workup

  1. stirringthe mixture was stirred for a further 72 hours
  2. washThe organic solution was washed with saturated aqueous sodium bicarbonate
  3. dry with materialwith 1N hydrochloric acid, dried with magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customto give an orange solid which
  7. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-faea5264efeb4494b351e920943d9dba
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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