Dimethylformamide dimethyl acetal → HCID 54139288, compound

HRID 258164Notes

Reaction equation

HRID 258164 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:26][C:27]1([CH3:46])[C:31](=[CH2:32])[S:30][C:29]([S:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[CH2:41][C:42]([O:44][CH3:45])=[O:43])=[N:28]1>>[CH3:6][N:4]([CH3:5])[CH:3]=[C:41]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[CH2:34][S:33][C:29]1[S:30][C:31](=[CH2:32])[C:27]([CH3:26])([CH3:46])[N:28]=1)[C:42]([O:44][CH3:45])=[O:43]

Participants

4

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11034602HCID 11034602, compound

Product 1

HCID 54139288HCID 54139288, compound

Procedure

This product (5.21 g), dimethylformamide dimethyl acetal (4.8 g) and pyridinium tosylate were heated together in a flask equipped with a Vigreaux column topped by a distillation head. The mixture was heated by an oil bath at 95° for 6 hours, causing the methanol produced by reaction to slowly distil off. The reaction mixture was then cooled, diluted with an aqueous solution of sodium hydrogen carbonate and extracted into ethyl acetate. The extract was washed with water, dried over magnesium sulphate and evaporated to give an oil which was purified by column chromatography (stationary phase: silica, eluent: 4:1 hexane:ethyl acetate) to give methyl 3-dimethylamino-2-[α-(4,4-dimethyl-5-methylene-2-thiazolin-2-ylthio)-o-tolyl]prop-2-enoate. (Compound 13A)

Workup

  1. customequipped with a Vigreaux column
  2. temperatureThe mixture was heated by an oil bath at 95° for 6 hours
  3. customproduced by reaction
  4. customto slowly distil off
  5. temperatureThe reaction mixture was then cooled
  6. additiondiluted with an aqueous solution of sodium hydrogen carbonate
  7. extractionextracted into ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. customto give an oil which
  12. customwas purified by column chromatography (stationary phase: silica, eluent: 4:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-e6d5341aa71e47828b8404242d724558
Source dataset
uspto-grants-1993_11
Patent number
US05264609

Reaction notes

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