Salicylamide → HCID 11682447, compound

HRID 427282Notes

Reaction equation

HRID 427282 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(O[CH:14](OCC)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:19][CH:18]=1)C>C(Cl)(Cl)Cl>[O:9]=[C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4][CH:14]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:22]=2)[NH:10]1

Participants

4

Reactant 2

HCID 5147SalicylamideHCID 23298348HCID 23298348, compound

Product 1

HCID 11682447HCID 11682447, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of polyphosphonate ethyl ester (PPE) (3.15 g, 7.29 mmol) in chloroform (4.0 mL) was added salicylamide (0.5 g, 3.65 mmol) followed by addition of a solution of 5-[4-[(2,2-diethoxy)ethoxy]phenyl methyl]thiazolidin-2,4-dione (1.36 g, 4.0 mmol) obtained in example 2, in chloroform (10 mL) dropwise at 25-30° C. The reaction mixture was immersed in a preheated oil bath and refluxed for 3 h. The reaction mixture was cooled to room temperature and CHCl3 was removed under reduced pressure. To the resultant residue aq. sat. NaHCO3 solution (25 mL) was added and stirred for 30 min. at 25-30° C. The precipitated brown coloured solid was filtered and purified by column chromatography using EtOAc:pet. ether (1:1) to yield the title compound (1.15 g, 81%). mp: 134° C.-138° C.

Workup

  1. customThe reaction mixture was immersed in a preheated oil bath
  2. temperaturerefluxed for 3 h
  3. customCHCl3 was removed under reduced pressure
  4. additionTo the resultant residue aq. sat. NaHCO3 solution (25 mL) was added
  5. filtrationThe precipitated brown coloured solid was filtered
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-359284a9cdfb4d7bb1d6c40f12b2d0d0
Source dataset
uspto-grants-2001_11
Patent number
US06313113B1

Reaction notes

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