Oxalyl chloride → HCID 23141460, compound

HRID 646286Notes

Reaction equation

HRID 646286 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[C:14]([O-:16])=O.C(Cl)(=O)C(Cl)=O.[F:23][C:24]([F:34])([F:33])[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.C(N(CC)C(C)C)(C)C>ClCCl.CN(C)C=O>[F:23][C:24]([F:33])([F:34])[O:25][C:26]1[CH:27]=[CH:28][C:29]([NH:30][C:14](=[O:16])[C:4]2[CH:5]=[C:6]([CH:12]=[CH:13][C:3]=2[O:2][CH3:1])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 6008484-(Trifluoromethoxy)anilineHCID 23141414HCID 23141414, compound

Product 1

HCID 23141460HCID 23141460, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

1-Ethyl 4-methoxyisophthalate (150 mg) obtained in step D, and 3 μL of N,N-dimethylformamide were dissolved in 10 mL of dichloromethane, and the solution was cooled to 0° C. To this solution, 88 μL of oxalyl chloride was added little by little, and the mixture was stirred for 20 minutes at 0° C., followed by stirring the mixture for. 16 hours at room temperature. The reaction mixture was distilled under reduced pressure, and dried to obtain a light yellow solid. This solid was dissolved in 9 mL of dichloromethane, and 3 mL of the solution was added to a solution of 42 mg of 4-trifluoromethoxyaniline and 123 μL of N,N-diisopropylethylamine-dissolved in 2 mL of dichloromethane. The mixture was stirred for 6 hours at room temperature, and then dichloromethane was distilled off under reduced pressure. The resulting residue was purified by column chromatography (5 g of silica gel) using a 1:1 mixture of dichloromethane and n-hexane as an elution solvent, thereby obtaining 79 mg (92%) of ethyl N-(4-trifluoromethoxyphenyl)-4-methoxyisophthalamate.

Workup

  1. stirringby stirring the mixture for
  2. custom16 hours
  3. customat room temperature
  4. distillationThe reaction mixture was distilled under reduced pressure
  5. customdried
  6. customto obtain a light yellow solid
  7. stirringThe mixture was stirred for 6 hours at room temperature
  8. distillationdichloromethane was distilled off under reduced pressure
  9. customThe resulting residue was purified by column chromatography (5 g of silica gel)
  10. additiona 1:1 mixture of dichloromethane and n-hexane as an elution solvent

Sources & evidence

ORD record
ord-62d07f4b29594acbb78042635415eae9
Source dataset
uspto-grants-2010_04
Patent number
US07705053B2

Reaction notes

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