Ammonia → HCID 66574957, compound

HRID 1529173Notes

Reaction equation

HRID 1529173 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:8]=[C:9]2[C:15]([C:16]3[N:17]=[N:18][C:19]([C:23]([CH3:29])([CH3:28])[C:24]([O:26]C)=O)=[C:20](O)[N:21]=3)=[N:14][N:13]([CH2:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])[C:10]2=[N:11][CH:12]=1.[NH3:39]>C(#N)C>[F:6][C:7]1[CH:8]=[C:9]2[C:15]([C:16]3[N:17]=[N:18][C:19]4[C:23]([CH3:29])([CH3:28])[C:24](=[O:26])[NH:39][C:20]=4[N:21]=3)=[N:14][N:13]([CH2:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:34])([F:36])[F:35])[C:10]2=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178500135HCID 178500135, compound

Product 1

HCID 66574957HCID 66574957, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.172 ml of phosphoryl chloride were added to 290 mg (0.606 mmol) of the compound from Example 17A, and the mixture was stirred at RT overnight. The reaction mixture was dissolved in 40 ml of acetonitrile and, with ice-cooling, stirred into 27 ml of concentrated aqueous ammonia solution (33% strength). The mixture was stirred at room temperature for 2 days. The mixture was then concentrated. The residue was taken up in water and ethanol and treated in an ultrasonic bath. A precipitate was formed, which was filtered off with suction and washed with water, ethanol and then with diethyl ether. DMF was added to this residue, acetonitrile and water were added and the mixture was then once more filtered off with suction. The precipitate was washed with acetonitrile and water and then dried under high vacuum. This gave 149 mg of the title compound (52% of theory, purity 94%).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 2 days
  3. concentrationThe mixture was then concentrated
  4. additionethanol and treated in an ultrasonic bath
  5. customA precipitate was formed
  6. filtrationwhich was filtered off with suction
  7. washwashed with water, ethanol
  8. additionDMF was added to this residue, acetonitrile and water
  9. additionwere added
  10. filtrationthe mixture was then once more filtered off with suction
  11. washThe precipitate was washed with acetonitrile and water
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-204ce369ef434a0c993fe37155d97ad5
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

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