Water → HCID 118270793, compound

HRID 62633Notes

Reaction equation

HRID 62633 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11](S(C)(=O)=O)[C:10]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)([C:17]([F:20])([F:19])[F:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([C:21]2[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=2)([C:17]([F:20])([F:19])[F:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 118270849HCID 118270849, compound

Product 1

HCID 118270793HCID 118270793, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Benzyl-3-(3,5-dichlorophenyl)-4-(methylsulfonyl)-3-(trifluoromethyl)pyrrolidine (2.00 g, 95% purity, 4.13 mmol) was dissolved in toluene (40 mL) under a nitrogen atmosphere and sodium carbonate (1.31 g, 12.4 mmol) was added. The reaction mixture was heated to reflux for 150 minutes and cooled to room temperature. Water (20 mL) was added, the mixture stirred for 5 minutes and the phases separated. The water phase was extracted with toluene (20 mL) and solvent of the combined organic phases was evaporated under vacuum. The crude material was dissolved in warm n-heptane and after standing and cooling the forming crystals were filtered off to yield 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,3-dihydro-1H-pyrrole (972 mg, 95% purity, 60% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 150 minutes
  3. customthe phases separated
  4. extractionThe water phase was extracted with toluene (20 mL) and solvent of the combined organic phases
  5. customwas evaporated under vacuum
  6. dissolutionThe crude material was dissolved in warm n-heptane
  7. temperaturecooling the forming crystals
  8. filtrationwere filtered off

Sources & evidence

ORD record
ord-74c9bb4a37fe4328bd577506555eb244
Source dataset
uspto-grants-2016_09
Patent number
US09447036B2

Reaction notes

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