Ethylene Glycol → HCID 67170541, compound

HRID 1918342Notes

Reaction equation

HRID 1918342 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][O:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([Br:14])[C:11](Cl)=[N:10][CH:9]=1.[CH2:17]([OH:20])[CH2:18][OH:19]>>[C:4]([O:3][CH2:4][CH2:5][O:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([Br:14])[C:11]([O:19][CH2:18][CH2:17][O:20][C:7](=[O:6])[CH3:8])=[N:10][CH:9]=1)(=[O:3])[CH3:5]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 86672567HCID 86672567, compound

Product 1

HCID 67170541HCID 67170541, compound

Conditions

Temperature
60 °C

Procedure

Sodium hydride (1.29 g, 60% purity in mineral oil) was dissolved in ethylene glycol (25 ml) and the raw material of step 1 was added. This mixture was stirred at 60° C. for 1 h. Volatiles were evaporated at 95° C., 1 mbar. The remainder was suspended in pyridine (25 ml), acetic anhydride (25 g) was added slowly during 30 minutes with stirring and stirring continued for 1 h. The mixture was partitioned between ethyl acetate and water, the organic phase was washed with 2N HCl and saturated sodium bicarbonate solution, dried over sodium chloride and evaporated to dryness in vacuo.

Workup

  1. customVolatiles were evaporated at 95° C.
  2. additionacetic anhydride (25 g) was added slowly during 30 minutes
  3. stirringwith stirring
  4. stirringstirring
  5. waitcontinued for 1 h
  6. customThe mixture was partitioned between ethyl acetate and water
  7. washthe organic phase was washed with 2N HCl and saturated sodium bicarbonate solution
  8. dry with materialdried over sodium chloride
  9. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5873752f3b1a43b4a47a1f70f1fa21b3
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

Loading…