Dimethyl Sulfoxide → HCID 136110648, compound

HRID 1609002Notes

Reaction equation

HRID 1609002 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]#[N: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]#[N: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 178458821HCID 178458821, compound

Product 1

HCID 136110648HCID 136110648, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 15 mL of methyl sulfoxide were added in sequence, 1.2 g (3.4 mmol) of 2-propionyl-3-hydroxy-5-(N-cyanomethyl-3-oxo-(2H)-1,4-benzoxazin-6-yl)cyclohex-2-en-1-one, 0.42 g (4.4 mmol) of ethoxyamine hydrochloride an d 0.36 g (4.4 mmol) of anhydrous sodium acetate. The resulting mixture was stirred at ambient temperature for 5 and 1/2 hours, becoming a clear amber solution. The reaction mixture was diluted with 100 mL of 0.1N HCl and extracted twice with 30 mL portions of ether. The extracts were combined, washed with water, then aqueous sodium chloride, dried over MgSO4 and filtered. Evaporation off of the solvent gave the crude product as a light amber oil which solidified upon standing. The crude solid was triturated in warm ether and the product isolated by filtration as a tan solid. The product was recovered in a yield of 1.1 g (81 percent of theoretical) and melted at 156°-159° C.; 1H NMR(CDCl3): d1.05-1.41 (m, 6H, both --CCH2CH3 's), 2.57-3.62 (m, 7H), 4.17 (q, J=7 Hz, 2H,--OCH2CH3), 4.70 (s, 2H, --OCH2C=O), 4.88 (s, 2H, --NCH2CN), 6.92-7.20 (m, 3H, aromatic H's), 15.10 (broad s, 1H, enol H); (Compound 4).

Workup

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

Sources & evidence

ORD record
ord-c6751e9cda864f9bb6ef6ac5dcba21f0
Source dataset
uspto-grants-1995_03
Patent number
US05399542

Reaction notes

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