Dimethyl Sulfoxide → HCID 136040515, compound

HRID 1609001Notes

Reaction equation

HRID 1609001 reaction equation
CS(C)=O.[C:5]([C:9]1[C:10](=[O:28])[CH2:11][CH:12]([C:16]2[CH:17]=[CH:18][C:19]3[O:24][CH2:23][C:22](=[O:25])[N:21]([CH3:26])[C:20]=3[CH:27]=2)[CH2:13][C:14]=1[OH:15])(=O)[CH2:6][CH3:7].Cl.[CH2:30]([O:32][NH2:33])[CH3:31].C([O-])(=O)C.[Na+]>O>[CH2:30]([O:32][N:33]=[C:5]([C:9]1[C:10](=[O:28])[CH2:11][CH:12]([C:16]2[CH:17]=[CH:18][C:19]3[O:24][CH2:23][C:22](=[O:25])[N:21]([CH3:26])[C:20]=3[CH:27]=2)[CH2:13][C:14]=1[OH:15])[CH2:6][CH3:7])[CH3:31]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178458822HCID 178458822, compound

Product 1

HCID 136040515HCID 136040515, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20 mL of methyl sulfoxide were added in sequence, 1.0 g (3.0 mmol) of 2-propionyl-3-hydroxy-5-(N-methyl-3-oxo-(2H)-1,4-benzoxazin-6-yl)cyclohex-2-en-1-one, 0.37 g (3.9 mmol) of ethoxyamine hydrochloride and 0.32 g (3.9 mmol) of anhydrous sodium acetate. The resulting mixture was stirred at ambient temperature for 5 hours, becoming a clear amber solution. The reaction mixture was diluted with 100 mL of water and extracted twice with 30 mL portions of ether. The extracts were combined, washed with water, then aqueous sodium chloride and dried over MgSO4 and filtered. Evaporation off of the solvent gave the crude product as an oily residue which solidified upon standing. The crude solid was crushed and triturated in ether. The purified above-named product, as a tan solid, was recovered in a yield of 0.9 g (80 percent of theoretical). The title compound melted at 90°-92° C.; 1H NMR(CDCl3): d1.05-1.48 (m, 6H, both --CCH2CH3 's), 2.55-3.62 (m including s at 3.31 for --N--CH3, 1 OH) 4.18 (q, J=7 Hz, 2H,--OCH2CH3), 4.60 (s, 2H, --OCH2C=O), 6.82-7.13 (m, 3H, aromatic H's), 15.10 (broad s, 1H, enol H); (Compound 3).

Workup

  1. extractionextracted twice with 30 mL portions of ether
  2. washwashed with water
  3. dry with materialaqueous sodium chloride and dried over MgSO4
  4. filtrationfiltered
  5. customEvaporation off of the solvent

Sources & evidence

ORD record
ord-95d381f259f8452ea46f8541178284dc
Source dataset
uspto-grants-1995_03
Patent number
US05399542

Reaction notes

Loading…