Hydrochloric Acid → HCID 178482108, compound

HRID 967778Notes

Reaction equation

HRID 967778 reaction equation
[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+].[Cl-].C([NH+](CC)CC)C.Cl>CN1CCCC1=O>[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]2[NH:13][N:12]=[N:11][N:8]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 109645514-(Methylamino)benzonitrileHCID 12698378Triethylazanium chloride

Product 1

HCID 178482108HCID 178482108, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of the compound (450 mg) obtained in Step 1, 90% sodium azide (664 mg), triethylammonium chloride (703 mg) and anhydrous 1-methyl-2-pirrolidone (12 mL) was stirred at 140 to 160° C. for ten hours under nitrogen atmosphere. The reaction mixture was poured into ice-water, and the residue was adjusted to pH 3 with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was crystallized from tert-butyl methyl ether, collected by filtration and dried to obtain the titled compound (471 mg) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was crystallized from tert-butyl methyl ether
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-b38ebd0e5bfb4232a3c32e47e4a4c9ba
Source dataset
uspto-grants-2005_10
Patent number
US06956046B2

Reaction notes

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