Dichloromethane → 2-Hydroxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidine-4-one

HRID 51219

Reaction equation

HRID 51219 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.[NH2:38][OH:39]>CO.C(N(CC)CC)C>[OH:39][N:38]=[C:5]1[N:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3](=[O:15])[C:2]([CH3:1])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:6]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 443297Hydroxyamine hydrochlorideHCID 2723982Triethyloxonium tetrafluoroborateHCID 120563925-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one

Product 1

HCID 865884972-Hydroxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidine-4-oneYield 70.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

5-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one (0.3 g) was added to a 1M methylene chloride solution of triethyloxonium tetrafluoroborate (1 ml) at room temperature with stirring. After stirring the mixture for 24 hrs hydroxylamine hydrochloride (0.1 g) and triethylamine (0.3 g) in methanol (10 ml) were added at 0° C. The reaction mixture was again stirred for 2 hrs at room temperature followed by evaporation of the solvents under reduced pressure. The residue was added to ice water and then extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous ethyl acetate and the solvent was then evaporated under reduced pressure. The residue was purified by column chromatography (ethyl acetate-n-hexane, ½) to yield 2-hydroxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidine-4-one (0.21 g) having a melting point of 62-63° C.

Workup

  1. additionwere added at 0° C
  2. stirringThe reaction mixture was again stirred for 2 hrs at room temperature
  3. customfollowed by evaporation of the solvents under reduced pressure
  4. additionThe residue was added to ice water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate solution was dried over anhydrous ethyl acetate
  7. customthe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by column chromatography (ethyl acetate-n-hexane, ½)

Sources & evidence

ORD record
ord-bc5d0e561d0248559f5605bfeb83b1ff
Source dataset
uspto-grants-2004_03
Patent number
US06713629B2

Linked notes

Loading…