Dimethyl Sulfoxide → HCID 136026269, compound

HRID 1609007Notes

Reaction equation

HRID 1609007 reaction equation
CS(C)=O.[C:5]([C:9]1[C:10](=[O:30])[CH2:11][CH:12]([C:16]2[CH:17]=[CH:18][C:19]3[O:24][CH2:23][C:22](=[O:25])[N:21]([CH2:26][C:27]#[CH:28])[C:20]=3[CH:29]=2)[CH2:13][C:14]=1[OH:15])(=O)[CH2:6][CH3:7].Cl.[CH2:32]([O:34][NH2:35])[CH3:33].C([O-])(=O)C.[Na+]>Cl>[CH2:32]([O:34][N:35]=[C:5]([C:9]1[C:10](=[O:30])[CH2:11][CH:12]([C:16]2[CH:17]=[CH:18][C:19]3[O:24][CH2:23][C:22](=[O:25])[N:21]([CH2:26][C:27]#[CH:28])[C:20]=3[CH:29]=2)[CH2:13][C:14]=1[OH:15])[CH2:6][CH3:7])[CH3:33]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 178456564HCID 178456564, compound

Product 1

HCID 136026269HCID 136026269, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 50 mL of methyl sulfoxide were added in sequence 2.2 g (6.2 mmol ) of 2-propionyl-3-hydroxy-5-(N-(2-propynyl)-3-oxo-(2H)-1,4-benzoxazin-6-yl)cyclohex-2-en-1-one, 0.70 g (7.4 mmol) of ethoxyamine hydrochloride and 0.60 g (7.3 mmol) of anhydrous sodium acetate. The resulting mixture was stirred at ambient temperature for 3.5 hours. The reaction mixture was then diluted with 400 mL of 0.2N HCl and extracted four times with 20 mL portions of dichloromethane. The extracts were combined, washed with aqueous NaCl, dried over MgSO4 and filtered through a short pad of silica gel. Evaporation off of the solvent gave the crude product as a light yellow glass, which solidified upon standing. The solid was triturated in ether and the product isolated by filtration which afforded the above-named product as a white solid which melted at 100°-102° C. in a yield of 1.3 g (53 percent of theoretical). 1H NMR (CDCl3): d1.08-1.47 (m, 6H, both --CH2CH3 's), 2.31 (t, J=2 Hz, 1H,--C--CH), 2.62-3.64 (m, 7H), 4.17 (q, J=7 Hz, 2H, OCH2CH3), 4.67 (s, 2H, --OCH2C=O), 4.74(d, J=2 Hz, 2H,--NCH2), 6.87-7.12 (m, 3H, aromatic H's), 15.10 (broad s, 1H, enol H); (Compound 11).

Workup

  1. extractionextracted four times with 20 mL portions of dichloromethane
  2. washwashed with aqueous NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through a short pad of silica gel
  5. customEvaporation off of the solvent
  6. customgave the crude product as a light yellow glass, which
  7. customThe solid was triturated in ether
  8. customthe product isolated by filtration which

Sources & evidence

ORD record
ord-8a0d7e8d161d48d2837ecd61ca0020d2
Source dataset
uspto-grants-1995_03
Patent number
US05399542

Reaction notes

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