HCID 13105784, compound → HCID 13105795, compound

HRID 1758768Notes

Reaction equation

HRID 1758768 reaction equation
C(N1[C:12](=[O:13])C2=CC=CC=C2C1=S)C1C=CC=CC=1.CN1CCN([C:26]2[N:30]3[C:31]4[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:32]=4[CH:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[Cl:42])[O:34][CH2:35][C:29]3=[N:28][N:27]=2)CC1>C1C=CC=CC=1.ClCCl>[OH:13][CH2:12][C:26]1[N:30]2[C:31]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:32]=3[CH:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:42])[O:34][CH2:35][C:29]2=[N:28][N:27]=1

Participants

5

Reactant 2

HCID 13105784HCID 13105784, compoundHCID 57073352HCID 57073352, compound

Product 1

HCID 13105795HCID 13105795, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

N-Benzylthiophthalimide (1.62 g) is dissolved in benzene (74 ml) under heating. To the resulting solution is added a solution of Compound 18 (1.13 g) prepared in Example 10 in dichloromethane (10 ml), and the mixture is refluxed under heating for 15 hours, and concentrated. The residue is extracted with ethyl acetate and the extract is dried and concentrated. The residue is treated on column chromatography (silica gel/ethyl acetate) to give Compound 23 (0.7 g), which is recrystallized from ethyl acetate. Yield 47%

Workup

  1. temperatureunder heating
  2. temperaturethe mixture is refluxed
  3. temperatureunder heating for 15 hours
  4. concentrationconcentrated
  5. extractionThe residue is extracted with ethyl acetate
  6. customthe extract is dried
  7. concentrationconcentrated
  8. additionThe residue is treated on column chromatography (silica gel/ethyl acetate)

Sources & evidence

ORD record
ord-c9469ec30e604cfd97a9471828d71bdf
Source dataset
uspto-grants-1983_02
Patent number
US04374842

Reaction notes

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