Hydrochloric Acid → HCID 67916022, compound

HRID 1196249Notes

Reaction equation

HRID 1196249 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[CH:16]3[CH:12]([CH2:13][N:14](C(OC=C)=O)[CH2:15]3)[C:11](=[O:22])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1.C(OC(C)C)(C)C>[ClH:1].[Cl:29][C:25]1[CH:24]=[C:23]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH:16]3[CH:12]([CH2:13][NH:14][CH2:15]3)[C:11](=[O:22])[CH2:10][CH2:9]2)[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67915885(3aRS,7aRS)-7,7-bis(3-chlorophenyl)-2-vinyloxycarbonylperhydro-4-isoindolone

Product 1

HCID 67916022HCID 67916022, compoundYield 144.6%

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

(3aRS,7aRS)-7,7-Bis(3-chlorophenyl)-2-vinyloxycarbonylperhydro-4-isoindolone (1.5 g) is treated with a 6N solution (7.4 cc) of hydrochloric acid in dioxane for 2 hours at 25° C. The solution is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is heated for 1 hour in solution in ethanol at 60° C. and then stirred for 6 hours at 25° C. The solution is concentrated to dryness under reduced pressure (2.7 kPa) and the meringue-like product obtained solidified in isopropyl ether. The precipitate is drained and washed with isopropyl ether, then dried to give 7,7-bis(3-chlorophenyl)perhydro-4-isoindolone hydrochloride (1 g).

Workup

  1. concentrationThe solution is concentrated to dryness under reduced pressure (2.7 kPa)
  2. concentrationThe solution is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customthe meringue-like product obtained
  4. washwashed with isopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-1a38d43c30e5465eb2f1aa29c17cf4e7
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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