Water → HCID 2781632, compound

HRID 853080Notes

Reaction equation

HRID 853080 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-06e1ce8303b84e5a97f69f62cc30f284
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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