Dimethylformamide → HCID 9799569, compound

HRID 1827900Notes

Reaction equation

HRID 1827900 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 obtained in Step B 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 1 hour, the reaction mixture is hydrolysed using ice and is then extracted with ethyl acetate. After washing the organic phase with aqueous sodium hydroxide solution, it is dried over sodium sulphate and then evaporated in vacuo. Chromatography over silica gel (cyclohexane/acetone: 98/2) allows 0.42 g of the expected product to be obtained.

Workup

  1. waitAfter 1 hour
  2. extractionis then extracted with ethyl acetate
  3. washAfter washing the organic phase with aqueous sodium hydroxide solution, it
  4. dry with materialis dried over sodium sulphate
  5. customevaporated in vacuo
  6. customto be obtained

Sources & evidence

ORD record
ord-2cce901f616f4eecbe8fbe82adf2801e
Source dataset
uspto-grants-2006_06
Patent number
US07056929B2

Reaction notes

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