Hydrochloric Acid → HCID 59453382, compound

HRID 918763Notes

Reaction equation

HRID 918763 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:33]([F:36])([F:35])[F:34])[CH2:13][CH2:12][N:11]([C:14]3[CH:28]=[CH:27][C:17]([CH2:18][NH:19]C(=O)OC(C)(C)C)=[C:16]([C:29]([F:32])([F:31])[F:30])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:33]([F:36])([F:35])[F:34])[CH2:13][CH2:12][N:11]([C:14]3[CH:28]=[CH:27][C:17]([CH2:18][NH2:19])=[C:16]([C:29]([F:30])([F:31])[F:32])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 59453359HCID 59453359, compound

Product 1

HCID 59453382HCID 59453382, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture comprising t-butyl {4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-2-(trifluoromethyl)benzyl}carbamate (6.0 g), concentrated hydrochloric acid (20 mL) and ethanol (100 mL) was stirred at 50° C. for three hours. After cooling the mixture to room temperature, the reaction solution was diluted by adding water (150 mL) and ethyl acetate (150 mL). By adding sodium carbonate in small portions, the solution was neutralized. After the extraction using ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure to obtain the title compound (5.2 g).

Workup

  1. additionthe reaction solution was diluted
  2. extractionAfter the extraction
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-b33c518d2e2b468c98a400ed6f9f302f
Source dataset
uspto-grants-2016_03
Patent number
US09271499B2

Reaction notes

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