HCID 14800405, compound → HCID 14800406, compound

HRID 1681095Notes

Reaction equation

HRID 1681095 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([NH2:11])=O)=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[C:15]2[CH2:18][CH2:19][CH2:20][CH2:21][C:14]=2[C:13]1=[O:22]>S(Cl)(Cl)=O>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:11])=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[C:15]2[CH2:18][CH2:19][CH2:20][CH2:21][C:14]=2[C:13]1=[O:22]

Participants

3

Reactant 1

HCID 14800405HCID 14800405, compound

Product 1

HCID 14800406HCID 14800406, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To 30 ml of thionyl chloride, 1.13 g of N-(2-fluoro-4-chloro-5-aminocarbonylphenyl)-3,4,5,6-tetrahydrophthalimide was added and the mixture was heated to reflux under stirring for 16 hours. After cooling, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (silica gel, benzene/ethyl acetate=10/1 (v/v)) to obtain 0.63 g of the desired product.m.p.: 160°-162° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel, benzene/ethyl acetate=10/1 (v/v))

Sources & evidence

ORD record
ord-889c8a335c664c8cab0762e684a4f000
Source dataset
uspto-grants-1992_12
Patent number
US05169428

Reaction notes

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