Hydrochloric Acid → HCID 59453382, compound

HRID 1776981Notes

Reaction equation

HRID 1776981 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-0eb316f41f4245828382f333adeea923
Source dataset
uspto-grants-2016_02
Patent number
US09266830B2

Reaction notes

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