Reaction #79498

Reaction equation

5-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one

methylene chloride

triethyloxonium tetrahydroborate

Methoxyamine hydrochloride

→

2-methoxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one

Yield 41.9%

Solvents

methanol

triethylamine

Conditions

Workup

1. 1
   workup.WAITAfter 1 hr
2. 2
   Otherthe solvents were evaporated under reduced pressure
3. 3
   OtherThe residue was purified by column chromatography (chloroform)

Procedure

5-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one (0.87 g) was mixed with a 1M methylene chloride solution of triethyloxonium tetrahydroborate (3 ml) at room temperature. The reaction mixture was stirred overnight at room temperature. Methoxyamine hydrochloride (0.25 g) and triethylamine (0.61 g) in methanol (10 ml) were then added at room temperature to the mixture. After 1 hr. the solvents were evaporated under reduced pressure. The residue was purified by column chromatography (chloroform) to yield 2-methoxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one (0.38 g) having a melting point of 133-134° C.

Source