Ethylene Glycol → HCID 67170541, compound

HRID 1475753Notes

Reaction equation

HRID 1475753 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. The remainder was titurated in diethyl ether, cooled in an ice bath and filtered to yield 2.5 g of the title compound.

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
  10. temperaturecooled in an ice bath
  11. filtrationfiltered

Sources & evidence

ORD record
ord-176ba4106d8746be9e217cbfeca52e4f
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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