Potassium bisulfate → HCID 68139172, compound

HRID 1730247Notes

Reaction equation

HRID 1730247 reaction equation
S(=O)(=O)(O)[O-].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22](O)([CH2:23][CH3:24])[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:15]2=[O:26])=[C:10]([F:27])[CH:9]=1>C(Cl)(Cl)Cl>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22](=[CH:23][CH3:24])[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:15]2=[O:26])=[C:10]([F:27])[CH:9]=1

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 21496704HCID 21496704, compound

Product 1

HCID 68139172HCID 68139172, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

One part of potassium bisulfate and 25.3 parts of 2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-hydroxy-3-ethyl-1H-isoindol-1-one were heated with occasional stirring in an oil bath at 160°-170° for 15 minutes. The melt was poured into 200 parts of chloroform and washed successively with 100 parts of water, 50 parts of 10% aqueous sodium chloride solution and 100 parts of saturated aqueous sodium chloride solution. After drying the organic phase with anhydrous sodium sulfate, the solvent was evaporated at 300 mm. Hg at 50° to 22.3 parts of brown, glassy 2-(4-chloro-2-fluorophenyl) -2,3,4,5,6,7-hexahydro-3-ethylidene-1H-isoindol-1-one. The mixture of geometric isomers present was indicated by the absorption in the nuclear magnetic resonance spectrum of 5.1δ (1H, singlet vinyl proton) and 0.95δ (3H, singlet vinyl proton) and 1.3δ (1H, singlet vinyl proton) and 1.3δ (3H, singlet allylic methyl) for the isomer present in 40% of the total mixture.

Workup

  1. washwashed successively with 100 parts of water, 50 parts of 10% aqueous sodium chloride solution and 100 parts of saturated aqueous sodium chloride solution
  2. dry with materialAfter drying the organic phase with anhydrous sodium sulfate
  3. customthe solvent was evaporated at 300 mm. Hg at 50° to 22.3 parts of brown, glassy 2-(4-chloro-2-fluorophenyl) -2,3,4,5,6,7-hexahydro-3-ethylidene-1H-isoindol-1-one
  4. additionThe mixture of geometric isomers present
  5. customwas indicated by the absorption in the nuclear magnetic resonance spectrum of 5.1δ (1H, singlet vinyl proton) and 0.95δ (3H, singlet vinyl proton) and 1.3δ (1H, singlet vinyl proton) and 1.3δ (3H, singlet allylic methyl) for the isomer present in 40% of the total mixture

Sources & evidence

ORD record
ord-225f7db01e904171aa8ae65e17c3af10
Source dataset
uspto-grants-1976_11
Patent number
US03992189

Reaction notes

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