Diethylethanolamine → HCID 21432733, compound

HRID 2399107Notes

Reaction equation

HRID 2399107 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][OH:6])[CH3:2].[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[N:15][C:14]([C:20](Cl)=[O:21])=[CH:13]2>O1CCCC1>[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[N:15][C:14]([C:20]([O:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[O:21])=[CH:13]2

Participants

4

Reactant 2

HCID 7497DiethylethanolamineHCID 21432719HCID 21432719, compound

Product 1

HCID 21432733HCID 21432733, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-diethylaminoethanol (1.4 g.) in dry tetrahydrofuran (15 ml.) was added to a solution of 6-bromocinnolin-3-yl carbonyl chloride (1.07 g.) in dry tetrahydrofuran (15 ml.). The resulting solution was heated under reflux for 2 hours, and the solvent was then evaporated in vacuo. The solid residue was dissolved in water (50 ml.), the solution extracted with ethyl acetate (3× 100 ml.), and the combined extracts dried (MgSO4). The solution was evaporated to a small volume, petroleum ether (b.p. 60°-80° C.; 50 ml.) was added, the resulting mixture was filtered to give, as the solid residue, 2-diethylaminoethyl 6-bromocinnolin-3-yl carboxylate, m.p. 90°-93° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 2 hours
  3. customthe solvent was then evaporated in vacuo
  4. dissolutionThe solid residue was dissolved in water (50 ml.)
  5. extractionthe solution extracted with ethyl acetate (3× 100 ml.)
  6. dry with materialthe combined extracts dried (MgSO4)
  7. customThe solution was evaporated to a small volume, petroleum ether (b.p. 60°-80° C.; 50 ml.)
  8. additionwas added
  9. filtrationthe resulting mixture was filtered

Sources & evidence

ORD record
ord-124931ef764d47b083f1159437f5d3d6
Source dataset
uspto-grants-1977_05
Patent number
US04027023

Reaction notes

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