Thionyl Chloride → HCID 13503445, compound

HRID 485210Notes

Reaction equation

HRID 485210 reaction equation
[Cl: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:23](O)=[O:24])[CH2:21][CH3:22].S(Cl)(Cl)=O>>[Cl: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:23](=[O:24])[NH:8][CH2:5][CH2:4][CH3:3])[CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 15582905HCID 15582905, compound

Product 1

HCID 13503445HCID 13503445, compound

Procedure

A mixture of 2.00 g. of N-[4-chloro-3-(1-carboxypropoxy)phenyl]-3,4,5,6-tetrahydrophthalimide and 5 ml. of thionyl chloride was refluxed with stirring for 1 hour and excess thionyl chloride was distilled off under a reduced pressure. The product was dissolved in 10 ml. of toluene and a mixture of 0.36 g. of n-propylamine, 0.6 g. of triethylamine and 5 ml. of toluene was added and the mixture was stirred at room temperature for 2 hours. Chloroform was added and the resulting organic phase was washed with water and dried and the product was purified by a chromatography on a column of silica gel (developing solvent:chloroform) and recrystallized from a mixture of ethyl acetate and n-hexane to obtain 1.62 g. of Compound No. 286 shown in Table 1.

Workup

  1. additionA mixture of 2.00 g
  2. distillationexcess thionyl chloride was distilled off under a reduced pressure
  3. dissolutionThe product was dissolved in 10 ml
  4. additionof toluene and a mixture of 0.36 g
  5. additionof toluene was added
  6. stirringthe mixture was stirred at room temperature for 2 hours
  7. additionChloroform was added
  8. washthe resulting organic phase was washed with water
  9. customdried
  10. customthe product was purified by a chromatography on a column of silica gel (developing solvent:chloroform)
  11. customrecrystallized from a mixture of ethyl acetate and n-hexane
  12. customto obtain 1.62 g

Sources & evidence

ORD record
ord-d7ca8da244b943d896715f68c061b932
Source dataset
uspto-grants-1985_08
Patent number
US04536209

Reaction notes

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