Hydrochloric Acid → HCID 15582862, compound

HRID 485203Notes

Reaction equation

HRID 485203 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]([C:22]([O:24]CC)=[O:23])[CH3:21].[I-].[Li+].Cl>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]([C:22]([OH:24])=[O:23])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 15582850HCID 15582850, compound

Product 1

HCID 15582862HCID 15582862, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1 g. of N-[4-bromo-3-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 5 g. of lithium iodide and 120 ml. of anhydrous N,N-dimethylformamide was heated with stirring in nitrogen gas flow at 140° C. for 1.5 hours and the reaction mixture was cooled to room temperature and 2N-HCl was added and the product was extracted with ether. The extract was concentrated under a reduced pressure and the residue was recrystallized from a mixture of benzene-cyclohexane to obtain 0.72 g. of Compound No. 10 shown in Table 1.

Workup

  1. additionA mixture of 1 g
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionthe product was extracted with ether
  4. concentrationThe extract was concentrated under a reduced pressure
  5. customthe residue was recrystallized from a mixture of benzene-cyclohexane
  6. customto obtain 0.72 g

Sources & evidence

ORD record
ord-12f7e9c1195644e0ad8a63e468b133d0
Source dataset
uspto-grants-1985_08
Patent number
US04536209

Reaction notes

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