Triethylamine → HCID 11323074, compound

HRID 1166037Notes

Reaction equation

HRID 1166037 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][C:5]([NH2:15])=[C:4]([F:16])[CH:3]=1.C(N(CC)CC)C.Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([F:16])[C:5]([N:15]=[C:25]=[O:27])=[CH:6][C:7]=1[O:8][C:9]1[N:10]=[CH:11][CH:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 114478024-chloro-2-fluoro-5-(2-pyrimidinyloxy)aniline

Product 1

HCID 11323074HCID 11323074, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

4-Chloro-2-fluoro-5-(2-pyrimidinyloxy) benzenamine (2 g) and triethyl amine (1.7 g) were dissolved in anhydrous ethyl acetate (75 ml) and stirred under ice cooling. Triphosgene (2.5 g) dissolved in ethyl acetate (75 ml) was slowly added to the stirred solution. The solution was heated at reflux for 2 hr and filtered. Evaporation of the solvent afforded 2-(2-chloro-4-fluoro-5-isocyanatophenoxy)-pyrimidine which was used for the next step without further purification.

Workup

  1. additionwas slowly added to the stirred solution
  2. temperatureThe solution was heated
  3. temperatureat reflux for 2 hr
  4. filtrationfiltered
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f8ca67b821a14592bf5a5bff94c42778
Source dataset
uspto-grants-2003_09
Patent number
US06613718B2

Reaction notes

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