Ammonia → HCID 19874089, compound

HRID 2106895Notes

Reaction equation

HRID 2106895 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]1[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH:17]2[CH2:19][CH2:18]2)[N:11]=1.Cl.N>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]2[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH:17]3[CH2:19][CH2:18]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 97423-FluoroanilineHCID 19804698HCID 19804698, compound

Product 1

HCID 19874089HCID 19874089, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.5 g (50 mmol) of 3-fluoroaniline and 9.3 g (55 mmol) of 2-chloro-4-methyl-6-cyclopropylpyrimidine in 100 ml of ethanol is adjusted to pH 1 with 5 ml of concentrated hydrochloric acid with stirring, and is then heated under reflux for 18 hours. After the brown emulsion has been cooled to room temperature, it is rendered alkaline with 10 ml of 30% ammonia, poured onto 100 ml of ice-water and extracted twice with 150 ml of diethyl ether each time. The combined extracts are washed with 50 ml of water, dried over sodium sulfate and filtered, and the solvent is evaporated. The yellowish crystals which remain are purified by recrystallisation from diisopropyl ether/petroleum ether (b.p. 50°-70° C.). The white crystals melt at 87°-89° C.; yield: 8.3 g (34 mmol; 68% of the theoretical yield).

Workup

  1. temperatureis then heated
  2. temperatureunder reflux for 18 hours
  3. extractionextracted twice with 150 ml of diethyl ether each time
  4. washThe combined extracts are washed with 50 ml of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. customThe yellowish crystals which remain are purified by recrystallisation from diisopropyl ether/petroleum ether (b.p. 50°-70° C.)
  9. custommelt at 87°-89° C.
  10. custom68% of the theoretical yield)

Sources & evidence

ORD record
ord-9d11f43d481642599c9561f75378b819
Source dataset
uspto-grants-1990_06
Patent number
US04931560

Reaction notes

Loading…