Dimethylformamide → HCID 9799569, compound

HRID 1595210Notes

Reaction equation

HRID 1595210 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[O:24][C:23]([CH3:26])([CH3:25])[CH:22]=[CH:21][C:5]2=C2[C:15]=1[C:14](=[O:16])[C:13]1[CH:12]=[C:11]3[CH:17]=[CH:18][CH:19]=[CH:20][C:10]3=[CH:9]C=1N2.[H-].[Na+].S(OC)(O[CH3:33])(=O)=O.[CH3:36][N:37]([CH3:40])[CH:38]=O>>[CH3:33][O:1][C:2]1[CH:3]=[C:4]2[O:24][C:23]([CH3:26])([CH3:25])[CH:22]=[CH:21][C:5]2=[C:36]2[C:15]=1[C:14](=[O:16])[C:13]1[CH:12]=[C:11]3[CH:17]=[CH:18][CH:19]=[CH:20][C:10]3=[CH:9][C:38]=1[N:37]2[CH3:40]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 10665070HCID 10665070, compound

Product 1

HCID 9799569HCID 9799569, compound

Procedure

To a solution of 0.5 g of the product of Example 1 in 20 ml of anhydrous dimethylformamide there are slowly added at 0° C., under an inert atmosphere, 0.16 g of sodium hydride and then, after 15 minutes, 0.65 ml of dimethyl sulphate (6 equivalents). After one hour, the reaction mixture is poured onto ice and then extracted with ethyl acetate. The organic phase is washed with an aqueous sodium hydroxide solution and subsequently dried over sodium sulphate and then evaporated in vacuo. Chromatography on silica gel (cyclohexane/acetone: 98/2) allows 0.42 g of the expected product to be isolated.

Workup

  1. waitAfter one hour
  2. additionthe reaction mixture is poured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with an aqueous sodium hydroxide solution
  5. dry with materialsubsequently dried over sodium sulphate
  6. customevaporated in vacuo
  7. customto be isolated

Sources & evidence

ORD record
ord-c0edfc83749541bbb4b588fcab740eb4
Source dataset
uspto-grants-2001_09
Patent number
US06288073B1

Reaction notes

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