Triethylamine → 4-Chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl isocyanate

HRID 1862338Notes

Reaction equation

HRID 1862338 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[Cl:20][C:21]1[C:27]([O:28][C:29]2[C:30]([O:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[N:31][CH:32]=[CH:33][CH:34]=2)=[CH:26][C:24]([NH2:25])=[C:23]([F:41])[CH:22]=1>C(OCC)(=O)C>[Cl:20][C:21]1[C:27]([O:28][C:29]2[C:30]([O:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[N:31][CH:32]=[CH:33][CH:34]=2)=[CH:26][C:24]([N:25]=[C:2]=[O:4])=[C:23]([F:41])[CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 219335774-Chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}aniline

Product 1

HCID 186192764-Chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl isocyanateYield 98.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Into a solution of 227 mg of triphosgene in 8 ml of ethyl acetate, a solution of 155 mg of triethylamine and 250 mg of 4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}aniline in 8 ml of ethyl acetate was added at 0° C. The mixture was stirred for 30 minutes at the same temperature, then for 2 hours at reflux temperature. The reaction solution was filterated while it was hot, and the solvent was distilled off under reduced pressure to obtain 266 mg of 4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl isocyanate.

Workup

  1. temperaturefor 2 hours at reflux temperature
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b1805c177b4c4ac8820eba42051ba416
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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