Triethylamine → HCID 22340996, compound

HRID 584553Notes

Reaction equation

HRID 584553 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-ce5e81857d44447cbc2122c90459c79b
Source dataset
uspto-grants-2005_08
Patent number
US06927193B2

Reaction notes

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