Ammonia → HCID 56597346, compound

HRID 1505470Notes

Reaction equation

HRID 1505470 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:8]=1[CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]([C:19]2[N:20]=[N:21][C:22]([C:26]([CH3:32])([CH3:31])[C:27]([O:29]C)=O)=[C:23](O)[N:24]=2)=[N:11]1.[NH3:38]>C(#N)C>[F:6][C:7]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:8]=1[CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]([C:19]2[N:20]=[N:21][C:22]3[C:26]([CH3:32])([CH3:31])[C:27](=[O:29])[NH:38][C:23]=3[N:24]=2)=[N:11]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178500131HCID 178500131, compound

Product 1

HCID 56597346HCID 56597346, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

29 ml of phosphoryl chloride were added to 2.74 g (6.221 mmol) of the compound from Example 77A, and the mixture was stirred at RT overnight. The reaction mixture was then taken up in 430 ml of acetonitrile and, with ice cooling, stirred into 260 ml of concentrated ammonia solution (33% in water). The mixture was stirred at room temperature overnight and then concentrated on a rotary evaporator. The residue was stirred with water and ethyl acetate and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution and then dried over sodium sulphate, filtered and concentrated on a rotary evaporator. The residue was stirred with ethyl acetate and diethyl ether. A solid was filtered off with suction and then washed with diethyl ether and ethyl acetate. Drying under high vacuum gave 2.13 g of the title compound in a purity of 94% (79% of theory).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationconcentrated on a rotary evaporator
  3. stirringThe residue was stirred with water and ethyl acetate
  4. extractionthe aqueous phase was extracted twice with ethyl acetate
  5. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator
  9. stirringThe residue was stirred with ethyl acetate and diethyl ether
  10. filtrationA solid was filtered off with suction
  11. washwashed with diethyl ether and ethyl acetate
  12. customDrying under high vacuum

Sources & evidence

ORD record
ord-18b8ec0b6752428da50b248350a2b9ce
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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