Water → HCID 118270793, compound

HRID 62634Notes

Reaction equation

HRID 62634 reaction equation
[Cl-].[CH2:2]([NH+:9]1[CH2:13][CH:12](S(C2C=CC=CC=2)=O)[C:11]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)([C:22]([F:25])([F:24])[F:23])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1>[CH2:2]([N:9]1[CH:13]=[CH:12][C:11]([C:26]2[CH:27]=[C:28]([Cl:33])[CH:29]=[C:30]([Cl:32])[CH:31]=2)([C:22]([F:25])([F:24])[F:23])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 118270162HCID 118270162, compound

Product 1

HCID 118270793HCID 118270793, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoromethyl)pyrrolidinium chloride (1.00 g, 82% purity, 1.53 mmol) is suspended in toluene (3 mL) under a nitrogen atmosphere. Sodium carbonate (810 mg, 7.65 mmol) was added and the mixture was heated to reflux for 2.5 hours. After cooling water was added, the phases were separated and the aqueous phase was extracted twice with toluene. The combined organic phases were dried over sodium sulphate, filtered and the solvent evaporated. The residue was repeatedly crystallized from n-heptane to yield 1-benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,3-dihydro-1H-pyrrole (198 mg, 89% purity, 31% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. additionwas added
  4. customthe phases were separated
  5. extractionthe aqueous phase was extracted twice with toluene
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customThe residue was repeatedly crystallized from n-heptane

Sources & evidence

ORD record
ord-b25c7d05d89f4b2198d1d7a8ca2943a3
Source dataset
uspto-grants-2016_09
Patent number
US09447036B2

Reaction notes

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