Dichloromethane → 2-(4-Chlorophenyl)imino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one

HRID 1016544Notes

Reaction equation

HRID 1016544 reaction equation
[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:6][C:5](=S)[N:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15].C(Cl)Cl.F[B-](F)(F)F.C([O+](CC)CC)C.[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1>C(Cl)(Cl)Cl.O>[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([N:42]=[C:5]2[N:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:3](=[O:15])[C:2]([CH3:1])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:6]2)=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 78124-ChloroanilineHCID 2723982Triethyloxonium tetrafluoroborateHCID 120563925-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one

Product 1

HCID 120563992-(4-Chlorophenyl)imino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-oneYield 57.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

5-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one (0.28 g) was mixed with a 1M methylene chloride solution of triethyloxonium tetrafluoroborate (1 ml) at room temperature. The reaction mixture was stirred for 24 hrs at room temperature then p-chloroaniline (0.25 g) in chloroform (10 ml) was added to the mixture at 0° C. The mixture was stirred at room temperature for 1 hr and then water was added. The separated oil was extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (chloroform-n-hexane, 1/1) to yield 2-(4-chlorophenyl)imino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one (0.21 g) having a melting point of 53-54° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hr
  2. extractionThe separated oil was extracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (chloroform-n-hexane, 1/1)

Sources & evidence

ORD record
ord-105d2b56416140af9ee08bc5a39791ea
Source dataset
uspto-grants-2002_11
Patent number
US06476055B1

Reaction notes

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