Diphosgene → (3-Chloro-phenyl)-methyl-carbamic Acid 4-trifluoromethyl-pyrimidin-2-yl Ester

HRID 1831244Notes

Reaction equation

HRID 1831244 reaction equation
[O:1]=[C:2](Cl)[O:3][C:4](Cl)(Cl)Cl.[F:9][C:10]([F:19])([F:18])[C:11]1[CH:16]=[CH:15][N:14]=C(O)[N:12]=1.[Cl:20][C:21]1[CH:22]=[C:23]([NH:27][CH3:28])[CH:24]=[CH:25][CH:26]=1>O1CCCC1>[F:9][C:10]([F:19])([F:18])[C:11]1[CH:16]=[CH:15][N:14]=[C:4]([O:3][C:2](=[O:1])[N:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[CH:22]=2)[CH3:28])[N:12]=1

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 1389003-chloro-N-methylanilineHCID 178517744HCID 178517744, compound

Product 1

HCID 69517834(3-Chloro-phenyl)-methyl-carbamic Acid 4-trifluoromethyl-pyrimidin-2-yl EsterYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C. diphosgene (0.99 g, 5.00 mmol) was added to a stirred solution of 4-trifluoromethyl-2-hydroxypyrimidine (1.64 g, 10.0 mmol) in tetrahydrofuran (25 ml). The cooling bath was removed and stirring was continued at room temperature for 1 hour. (3-Chlorophenyl)-methylamine (0.35 g, 2.50 mmol) was added to one-fourth of the solution. After stirring overnight at room temperature the solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (20:80)) followed by preparative HPLC, yielding the title compound (332 mg, 40%) as a colourless oil.

Workup

  1. customThe cooling bath was removed
  2. stirringAfter stirring overnight at room temperature the solvent
  3. customwas evaporated in vacuo
  4. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (20:80))

Sources & evidence

ORD record
ord-9030c78650774622ba859dd276ebdef4
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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