Water → HCID 2781632, compound

HRID 585846Notes

Reaction equation

HRID 585846 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].[H-].[Na+].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].O>COCCOC>[CH2:19]([O:18][C:16](=[O:17])[NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[O:3][C:2]([F:11])([F:12])[F:1])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 737542-(Trifluoromethoxy)aniline

Product 1

HCID 2781632HCID 2781632, compoundYield 115.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-5 °C

Procedure

2-(Trifluoromethoxy)aniline (50 g, 0.282 mol) was dissolved in DME (1000 mL) and cooled to −5° C. Sodium hydride (12.3 g, 55%, 0.282 mol) was added in portions and the suspension was allowed to warm to room temperature. Ethyl chloroformate (23.5 mL, 0.245 mol) was added drop by drop and the mixture was stirred for 2 h at room temperature and for 1.5 h at reflux after addition was complete. Hydrolysis was with water (110 mL). The phases were separated and the water phase was extracted with ethyl acetate. The organic phases were washed with brine, pooled and dried with MgSO4. Evaporation of the solvent yielded 70.6 g of a brown oil, which was purified by chromatography on silica gel with hexane/ethyl acetate (6:1). This yielded the title compound, (44.2 g, 62%) as a beige yellow oil. (EI-MS: m/e=249.1 (M+))

Workup

  1. temperatureto warm to room temperature
  2. temperatureat reflux
  3. additionafter addition
  4. customHydrolysis
  5. customThe phases were separated
  6. extractionthe water phase was extracted with ethyl acetate
  7. washThe organic phases were washed with brine
  8. dry with materialdried with MgSO4
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f2f0096c1e6948c0b322b9f7c5134517
Source dataset
uspto-grants-2005_08
Patent number
US06933387B2

Reaction notes

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