Ammonia → HCID 431947, compound

HRID 267368Notes

Reaction equation

HRID 267368 reaction equation
[NH3:1].[Cl-].[NH4+].Cl[C:5]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][N:8]=[CH:7][N:6]=1>C(O)C>[NH2:1][C:5]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][N:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 21557075HCID 21557075, compound

Product 1

HCID 431947HCID 431947, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 125 ml. of absolute ethanol saturated with ammonia was added 2.0 g. ammonium chloride and 25.7 g. (0.124 mol) of 4-chloro-5-phenoxy pyrimidine and the mixture was heated in a 250 ml. stainless steel pressure bomb at 160° for six hrs. The bomb was cooled and the contents poured into a 1000 ml. rb flask. The bomb was rinsed with 4 × 100 ml. boiling ethanol and the combined ethanol solutions were stripped to an oily mixture on the rotary evaporator. The residues were extracted with 4 × 150 ml ether and the ether solution concentrated on the steam bath until a solid began to precipitate. Cooling gave a yellow solid which was collected by vacuum filtration. The solid was taken up in hot ethyl acetate and treated with activated charcoal filtered and concentrated on the steam bath. Careful addition of hexane and cooling gave 15.3 g (66%) white crystals mp 118°-120°.

Workup

  1. temperatureThe bomb was cooled
  2. additionthe contents poured into a 1000 ml
  3. washThe bomb was rinsed with 4 × 100 ml
  4. customboiling ethanol and the combined ethanol solutions were stripped to an oily mixture on the rotary evaporator
  5. extractionThe residues were extracted with 4 × 150 ml ether
  6. concentrationthe ether solution concentrated on the steam bath until a solid
  7. customto precipitate
  8. temperatureCooling
  9. customgave a yellow solid which
  10. filtrationwas collected by vacuum filtration
  11. additiontreated with activated charcoal
  12. filtrationfiltered
  13. concentrationconcentrated on the steam bath
  14. additionCareful addition of hexane
  15. temperaturecooling

Sources & evidence

ORD record
ord-a97baa30d8544fcc8690091840cd06d8
Source dataset
uspto-grants-1976_03
Patent number
US03941889

Reaction notes

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