Hydrochloric Acid → HCID 22313860, compound

HRID 1384866Notes

Reaction equation

HRID 1384866 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C:7](=[O:12])[N:6]([CH2:13][CH:14]1[O:23][CH2:22][CH2:21][C:16]3(OCC[O:17]3)[CH2:15]1)[C:5]2=[O:24].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C:7](=[O:12])[N:6]([CH2:13][CH:14]1[CH2:15][C:16](=[O:17])[CH2:21][CH2:22][O:23]1)[C:5]2=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22313870HCID 22313870, compound

Product 1

HCID 22313860HCID 22313860, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

5,6-Dichloro-2-(1,4,8-trioxa-spiro[4.5]dec-7-ylmethyl)-isoindole-1,3-dione (87 mg, 0.23 mmol) was dissolved in tetrahydrofuran (2.5 ml). 1.0 N hydrochloric acid (1.0 ml) was added to the solution and the mixture was heated at 75° C. for 20 h. The heterogeneous mixture was evaporated to dryness in vacuo and the resulting solid was dissolved in dichloromethane (10 ml) and washed with water (3×2 ml). The organic layer was dried (MgSO4), filtered and the solvent evaporated in vacuo affording 62.1 mg (81%) of 5,6-dichloro-2-(4-oxo-tetrahydro-pyran-2-ylmethyl)-isoindole-1,3-dione as a solid.

Workup

  1. customThe heterogeneous mixture was evaporated to dryness in vacuo
  2. dissolutionthe resulting solid was dissolved in dichloromethane (10 ml)
  3. washwashed with water (3×2 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-89318fe69aa248b6af6555fb43cc5c2c
Source dataset
uspto-grants-2001_07
Patent number
US06262044B1

Reaction notes

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