N-Isopropylhydroxylamine Hydrochloride → HCID 53808329, compound

HRID 486102Notes

Reaction equation

HRID 486102 reaction equation
Cl.[CH:2]([NH:5][OH:6])([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[CH3:13][C:14]([C:17]1[CH:18]=[C:19]([CH:28]=[C:29]2[S:33][C:32](SC)=[N:31][C:30]2=[O:36])[CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])([CH3:16])[CH3:15]>C(O)C>[CH3:16][C:14]([C:17]1[CH:18]=[C:19]([CH:28]=[C:29]2[S:33][C:32]([N:5]([OH:6])[CH:2]([CH3:4])[CH3:3])=[N:31][C:30]2=[O:36])[CH:20]=[C:21]([C:24]([CH3:25])([CH3:26])[CH3:27])[C:22]=1[OH:23])([CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 170873N-Isopropylhydroxylamine HydrochlorideHCID 23665647Potassium tert-butoxideHCID 53858627HCID 53858627, compound

Product 1

HCID 53808329HCID 53808329, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-isopropylhydroxylamine hydrochloride (5.5 g, 0.049 mole), potassium-t-butoxide (4.83 g, 0.043 mole), and ethanol (500 mL) is stirred at room temperature for 15 minutes. 5-[(3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylene]-2-(methylthio)-4(5H)-thiazolone (7.27 g, 0.02 mole) is then added and the mixture is refluxed with stirring for six hours. After removal of the solvent under reduced pressure, the cooled reaction mixture is poured into a mixture of ice-water containing 1N hydrochloric acid and extracted with ether. The organic layer is washed with water, dried, and the solvent is evaporated to give 7.7 g of a residue. The residue is flash chromatographed on silica gel (202 g), eluting first with methylene chloride and then with methylene chloride-methanol (9:1) to give 7.0 purified product. It is recrystallized from methylene chloride-ethyl acetate-ether to give 4.2 g (54%) of pure 5-[[3,5-Bis-(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-]hydroxy(1-methylethyl)amino]-4(5 H)-thiazolidinone, (Z)-, mp 208° C. (dec).

Workup

  1. temperaturethe mixture is refluxed
  2. stirringwith stirring for six hours
  3. customAfter removal of the solvent under reduced pressure
  4. customthe cooled reaction mixture
  5. extractionextracted with ether
  6. washThe organic layer is washed with water
  7. customdried
  8. customthe solvent is evaporated

Sources & evidence

ORD record
ord-110622d8e5784d39a3d4d9ce932c50da
Source dataset
uspto-grants-1994_03
Patent number
US05290800

Reaction notes

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