Hydrochloric Acid → HCID 178469352, compound

HRID 1521846Notes

Reaction equation

HRID 1521846 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH2:15]([O:17][C:18]([C:20]#[C:21][C:22](OCC)=[O:23])=[O:19])[CH3:16].Cl>C(O)C.O>[OH:23][C:22]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:20]([C:18]([O:17][CH2:15][CH3:16])=[O:19])[CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 11430Potassium CarbonateHCID 69803Diethyl acetylenedicarboxylate

Product 1

HCID 178469352HCID 178469352, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of phenyl hydrazine (10 g, 92.6 mmol) in absolute ethanol (100 mL) is added dry K2CO3 (15.3 g, 111 mmol) and followed by slow addition of diethylacetylene dicarboxylate (10.6 g, 62.03 mmol) and the reaction mixture is heated at 85° C. for 12 h. The reaction mixture is then cooled to rt and 38 mL of 6N HCl is added dropwise. The reaction mixture is diluted with 150 mL water, extracted with ethylacetate. The organic layer is washed with water twice, dried over Na2SO4 and concentrated under vacuum. The residue is triturated with MTBE and the solid formed is filtered, washed with MTBE and dried to afford the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 12.12 (bs, 1H), 7.72-7.70 (m, 2H), 7.51-7.47 (m, 2H), 7.37-7.34 (m, 1H), 5.93 (s, 1H), 4.26 (q, J=4.1 Hz, 2H), 1.27 (t, J=7.1 Hz, 3H). MS (ESI+): 233.2.

Workup

  1. temperatureThe reaction mixture is then cooled to rt
  2. extractionextracted with ethylacetate
  3. washThe organic layer is washed with water twice
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue is triturated with MTBE
  7. customthe solid formed
  8. filtrationis filtered
  9. washwashed with MTBE
  10. customdried

Sources & evidence

ORD record
ord-2a2ee51d87f64f7389de0563c20cb1e9
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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