Ammonia → HCID 56598508, compound

HRID 1505468Notes

Reaction equation

HRID 1505468 reaction equation
P(Cl)(Cl)(Cl)=O.F[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][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])[C:10]2=[N:11][CH:12]=1.[NH3:38].[Cl-].[Na+]>C(#N)C>[F:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][N:13]1[C:10]2=[N:11][CH:12]=[CH:7][CH:8]=[C:9]2[C:15]([C:16]2[N:17]=[N:18][C:19]3[C:23]([CH3:28])([CH3:29])[C:24](=[O:26])[NH:38][C:20]=3[N:21]=2)=[N:14]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 24813Phosphorus oxychlorideHCID 178500126HCID 178500126, compound

Product 1

HCID 56598508HCID 56598508, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

50 ml of phosphoryl chloride were added to 9.700 g (22.025 mmol) of the compound from Example 61A, and the mixture was stirred at RT overnight. The reaction mixture was dissolved in 150 ml of acetonitrile and, with ice cooling, stirred into a mixture of 1337 ml of concentrated aqueous ammonia solution (35% strength) and 1300 ml of acetonitrile. The mixture was stirred at room temperature for 2 days. 300 g of sodium chloride were then added. Two phases formed. The organic phase was separated off and concentrated to dryness. The residue was taken up in ethyl acetate (150 ml). A precipitate formed and was filtered off with suction through a frit. The filter cake was washed three times with water and then three times with ethyl acetate (5 ml). The residue was dried under high vacuum. This gave 4.58 g (51% of theory) of the title compound.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 days
  2. customTwo phases formed
  3. customThe organic phase was separated off
  4. concentrationconcentrated to dryness
  5. customA precipitate formed
  6. filtrationwas filtered off with suction through a frit
  7. washThe filter cake was washed three times with water
  8. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-612b0d893ff0490f89feb82b56a026fd
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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