Triethylamine → HCID 178498589, compound

HRID 1183167Notes

Reaction equation

HRID 1183167 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3](OC)=[O:4].Cl.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][NH2:20].C(N(CC)CC)C>CO>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[C:3]([OH:4])=[CH:2][C:1]([C:7]([O:9][CH3:10])=[O:8])=[N:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12980Dimethyl acetylenedicarboxylateHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)

Product 1

HCID 178498589HCID 178498589, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl acetylenedicarboxylate (87.4 g, 757 mmol) was added to a solution of 2-fluoro-phenylhydrazine hydrochloride (100 g, 615 mmol) in methanol (1 l) at 0° C. Then triethylamine (125 g, 1.23 mol) was added slowly during 60 min. The solution was stirred for 16 h at room temperature, the solvent then removed under reduced pressure and the residue dissolved in EA (500 ml). After washing with aqueous hydrochloric acid (500 ml), the solvent was removed under reduced pressure. The title compound was obtained as an almost white solid in quantitative yield.

Workup

  1. customthe solvent then removed under reduced pressure
  2. dissolutionthe residue dissolved in EA (500 ml)
  3. washAfter washing with aqueous hydrochloric acid (500 ml)
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6db2fd99c6c54cc6b1ec49d068f51a94
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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