Ammonium Chloride → HCID 23120650, compound

HRID 490145Notes

Reaction equation

HRID 490145 reaction equation
C([Li])(C)(C)C.C(O[C:11](=[O:24])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=1)(C)(C)C.[O:25]=[C:26]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][C:39]([F:42])([F:41])[F:40])C(OCC)=O.[Cl-].[NH4+]>C(OCC)(=O)C.O1CCCC1.C(OCC)C.CCCCCCC>[Cl:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[C:20]([F:21])([F:22])[F:23])[NH:12][C:11](=[O:24])[C:26]2([OH:25])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][C:39]([F:40])([F:41])[F:42]

Participants

9

Reactant 4

HCID 25517Ammonium ChlorideHCID 10753918HCID 10753918, compoundHCID 21905863HCID 21905863, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 23120650HCID 23120650, compoundYield 64.1%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
-40 °C

Procedure

21 mL of a heptane solution of 1.6 mol/L tert-butyllithium was added dropwise under −78° C. cooling to a 30 mL diethyl ether solution of 4.00 g of tert-butyl[4-chloro-3-(trifluoromethyl)phenyl]carbamate, and the reaction mixture was stirred for 1 hour. The temperature was then raised to −40° C., and the reaction mixture was stirred for 2.5 hours at that temperature. The reaction mixture was cooled back down to −78° C., a 15 mL tetrahydrofuran solution of 4.25 g of ethyl oxo[2-(trifluoromethoxy)phenyl]acetate was added dropwise, and the reaction mixture was stirred for 2 hours at the same temperature. The temperature was then raised to room temperature, and the reaction mixture was stirred for 15 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was washed with saturated brine and dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/4; v/v) to obtain 3.57 g of the titled compound (colorless powder).

Workup

  1. stirringthe reaction mixture was stirred for 2.5 hours at that temperature
  2. temperatureThe reaction mixture was cooled back down to −78° C.
  3. stirringthe reaction mixture was stirred for 2 hours at the same temperature
  4. temperatureThe temperature was then raised to room temperature
  5. stirringthe reaction mixture was stirred for 15 hours
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/4; v/v)

Sources & evidence

ORD record
ord-8b5db7d3bbe24e9da78d167222af4dca
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

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