Ethylene Glycol → HCID 86672567, compound

HRID 1475752Notes

Reaction equation

HRID 1475752 reaction equation
[Br:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH2:12]([OH:15])[CH2:13][OH:14]>ClCCl>[OH:14][CH2:13][CH2:12][O:15][C:7](=[O:8])[C:6]1[CH:10]=[C:2]([Br:1])[C:3]([Cl:11])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 12677294HCID 12677294, compound

Product 1

HCID 86672567HCID 86672567, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-6-chloro-nicotinoyl chloride (W. J. Thompson et al., J. Org. Chem. 49 (1984), 5237-5243, raw material; 7.00 g, apx 50% purity) was diluted with dichloromethane (50 ml), ethylenglycol (17 g) was added slowly and the mixture was stirred at room temperature over night. The mixture was partitioned between ether and water and the aqueous phase was extracted three times with ether. Each ether extract was washed with new water. The combined organic layers were dried over sodium chloride and evaporated to dryness in vacuo to yield the title compound (6.0 g) as raw material.

Workup

  1. additionwas added slowly
  2. customThe mixture was partitioned between ether and water
  3. extractionthe aqueous phase was extracted three times with ether
  4. extractionEach ether extract
  5. washwas washed with new water
  6. dry with materialThe combined organic layers were dried over sodium chloride
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-c8c0b9bc7adf4fd8b03ef98ac25a2353
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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