Triethylamine → HCID 22340996, compound

HRID 1166035Notes

Reaction equation

HRID 1166035 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.[C:24](Cl)(Cl)=[S:25]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([F:16])[C:5]([N:15]=[C:24]=[S:25])=[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 10040ThiophosgeneHCID 114478024-chloro-2-fluoro-5-(2-pyrimidinyloxy)aniline

Product 1

HCID 22340996HCID 22340996, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

4-Chloro-2-fluoro-5-(2-pyrimidinyloxy)-benzenamine (50 g) and triethyl amine (42.2 g) were dissolved in anhydrous ethyl acetate (400 ml) and stirred under ice cooling. Thiophosgene (74.3 g) dissolved in ethyl acetate (400 ml) was slowly added to the stirred solution. The mixture was heated at reflux for 2 hr and filtered. Evaporation of the solvent afforded 2-(2-chloro-4-fluoro-5-isothiocyanatophenoxy)-pyrimidine which was used for the next step without purification. 1H NMR, CDCl3, 7.12 (1H, t, J=4.7 Hz), 7.13 (1H, d, J=7.0 Hz), 7.32 (1H, d, J=8.9 Hz), 8.58 (2H, t, J=4.7 Hz).

Workup

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

Sources & evidence

ORD record
ord-f8787ca8e2f74f6e93fa2ec77724f03b
Source dataset
uspto-grants-2003_09
Patent number
US06613718B2

Reaction notes

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