Methyl chloroformate → HCID 19082086, compound

HRID 963294Notes

Reaction equation

HRID 963294 reaction equation
[Cl:1][C:2]1[C:3]([CH2:29][CH3:30])=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:28])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=2)=[CH:13][CH:12]=1.[H-].[Na+].Cl[C:34]([O:36][CH3:37])=[O:35]>O1CCCC1>[Cl:1][C:2]1[C:3]([CH2:29][CH3:30])=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([C:34]([O:36][CH3:37])=[O:35])[C:9](=[O:28])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][N:19]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 19082084HCID 19082084, compound

Product 1

HCID 19082086HCID 19082086, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.87 g (2.0 mmol) of N-(3-chloro-2-ethylpyridin-4-yl)-4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetamide was dissolved in 5 ml of tetrahydrofuran, and the solution was stirred at room temperature. Then, 0.058 g (2.4 mmol) of sodium hydride was gradually added thereto, and the mixture was further stirred for one hour at room temperature. Then, 2 ml of a tetrahydrofuran solution containing 0.38 g (4.0 mmol) of methyl chloroformate was dropwise added thereto at a temperature of from -5° to 0° C, and the mixture was stirred for 30 minutes at a temperature of from -5° to 0° C. and for 12 hours at room temperature. Then, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) and then purified by high performance liquid chromatography to obtain 0.28 g of the desired product as a white powder (melting point: 62° to 64° C.)

Workup

  1. stirringthe mixture was further stirred for one hour at room temperature
  2. additionwas dropwise added
  3. stirringat a temperature of from -5° to 0° C, and the mixture was stirred for 30 minutes at a temperature of from -5° to 0° C. and for 12 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, ethyl acetate was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate)
  9. custompurified by high performance liquid chromatography

Sources & evidence

ORD record
ord-ca7d3b6f2be74eecb8f3058e7822a558
Source dataset
uspto-grants-1998_06
Patent number
US05763463

Reaction notes

Loading…