Hydroxyamine hydrochloride → 4-Hydroxyimino-5-methyl-5-phenyl-3-phenylamino-thiazolidine-2-thione

HRID 1016540Notes

Reaction equation

HRID 1016540 reaction equation
[NH:1]=[C:2]1[C:6]([CH3:13])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:5][C:4](=[S:14])[N:3]1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.N[OH:24]>CO>[OH:24][N:1]=[C:2]1[C:6]([CH3:13])([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:5][C:4](=[S:14])[N:3]1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 113928474-Imino-5-methyl-5-phenyl-3-phenylaminothiazolidine-2-thione

Product 1

HCID 865884954-Hydroxyimino-5-methyl-5-phenyl-3-phenylamino-thiazolidine-2-thioneYield 52.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-imino-5-methyl-5-phenyl-3-phenylaminothiazolidine-2-thione (0.31 g) and hydroxylamine hydrochloride (0.16 g) in methanol (15 ml) was refluxed for 6 hrs followed by solvent evaporation. The residue was purified by column chromatography (ethyl acetate-n-hexane, 1/3) to yield 4-hydroxyimino-5-methyl-5-phenyl-3-phenylamino-thiazolidine-2-thione (0.17 g) having a melting point of 83-84° C.

Workup

  1. customfollowed by solvent evaporation
  2. customThe residue was purified by column chromatography (ethyl acetate-n-hexane, 1/3)

Sources & evidence

ORD record
ord-9252920014404f7a818cb98457f706cc
Source dataset
uspto-grants-2002_11
Patent number
US06476055B1

Reaction notes

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