Dimethylformamide dimethyl acetal → HCID 67739543, compound

HRID 1721028Notes

Reaction equation

HRID 1721028 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:5](/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]=1.[CH3:20][O:21][CH:22](OC)N(C)C>>[CH3:20][O:21]/[CH:22]=[C:15](\[C:4]1[S:3][C:2]([CH3:1])=[N:6][C:5]=1[CH:7]=[CH:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)/[C:16]([O:18][CH3:19])=[O:17]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 22416960HCID 22416960, compound

Product 1

HCID 67739543HCID 67739543, compound

Procedure

A mixture of 3 g of the product of Step A and 30 ml of dimethylformamide dimethyl acetal was refluxed for 5 hours and then allowed to return to 25° C. The mixture was evaporated to dryness and the residue was dissolved in 30 ml of tetrahydrofuran and 5 ml of a 2N hydrochloric acid solution. After standing for 3 hours at 25° C., 10 ml of water were added, followed by decanting and extracting with methylene chloride. The organic phase was dried over magnesium sulfate, filtered and evaporated to dryness. The residue was dissolved in 50 ml of acetone and 6 g of potassium carbonate and then 12 ml of methyl iodide were added. The mixture was stirred for 16 hours at 20° to 25° C. and evaporated to dryness. The residue was chromatographed on silica, eluting with a hexane-ethyl acetate mixture (7-3) to obtain 1.8 g of the desired product. Thin layer chromatography; Rf= 0.20 [eluant: hexane-ethyl acetate (7-3)].

Workup

  1. temperaturewas refluxed for 5 hours
  2. customto return to 25° C
  3. customThe mixture was evaporated to dryness
  4. dissolutionthe residue was dissolved in 30 ml of tetrahydrofuran
  5. addition10 ml of water were added
  6. customby decanting
  7. extractionextracting with methylene chloride
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. dissolutionThe residue was dissolved in 50 ml of acetone
  12. addition6 g of potassium carbonate and then 12 ml of methyl iodide were added
  13. customevaporated to dryness
  14. customThe residue was chromatographed on silica
  15. washeluting with a hexane-ethyl acetate mixture (7-3)

Sources & evidence

ORD record
ord-adeb974c2b614cb08a04185e7a9539b2
Source dataset
uspto-grants-1996_04
Patent number
US05508414

Reaction notes

Loading…