Barium Carbonate → HCID 178440792, compound

HRID 2396804Notes

Reaction equation

HRID 2396804 reaction equation
Cl.[CH3:2][NH:3]O.C(=O)([O-])[O-:6].[Ba+2].[CH3:10][C:11]([C:14]1[CH:15]=[C:16]([CH:25]=[C:26]2[S:30][C:29](=S)[NH:28][C:27]2=[O:32])[CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])([CH3:13])[CH3:12]>C(O)C.O>[CH3:10][C:11]([C:14]1[CH:15]=[C:16]([CH:25]=[C:26]2[S:30][C:29]([NH:3][CH2:2][OH:6])=[N:28][C:27]2=[O:32])[CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 10563Barium CarbonateHCID 77906N-methylhydroxylamine hydrochlorideHCID 30715115-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinone

Product 1

HCID 178440792HCID 178440792, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of N-methylhydroxylamine hydrochloride (12.52 g, 0.15 mole), barium carbonate (14.8 g, 0.075 mole), ethanol (50 mL), and water (50 mL) is stirred at room temperature for ten minutes. 5-[(3,5-bis (1,1-dimethylethyl)-4-hydroxyphenyl)methylene]-2-thioxo-4-thiazolidinone (see Ikuo Katsumi et al Chem. Pharm. Bull., 34(4), 1619-1627 (1986)) (17.5 g, 0.05 mole) and ethanol (600 mL) are added to it and the resulting mixture is stirred and refluxed for 8 hours. The reaction mixture is then cooled, filtered, and the solvent is removed at 45° C. under reduced pressure. The residue is treated with ice-water and the resulting solid is separated by filtration, washed with water and extracted with methylene chloride. The organic layer is dried and concentrated to give 19 g of a residue. The residue is flash chromatographed over silica gel (214 g), eluting first with methylene chloride and then with methylene chloride-methanol (9:1) to give 11.5 g of the pure product. It is recrystallized from methanol-ethyl acetate, to give 8.6 g (48%) of 5-[[2,6-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-(hydroxymethylamino)-4(5H)-thiazolone,(Z)-, mp 199°-200° C. (dec).

Workup

  1. stirringthe resulting mixture is stirred
  2. temperaturerefluxed for 8 hours
  3. temperatureThe reaction mixture is then cooled
  4. filtrationfiltered
  5. customthe solvent is removed at 45° C. under reduced pressure
  6. additionThe residue is treated with ice-water
  7. customthe resulting solid is separated by filtration
  8. washwashed with water
  9. extractionextracted with methylene chloride
  10. customThe organic layer is dried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-5c1abcafebb34b42969fc0d04c825d98
Source dataset
uspto-grants-1996_02
Patent number
US05494927

Reaction notes

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