Hydrochloric Acid → HCID 178469350, compound

HRID 1766405Notes

Reaction equation

HRID 1766405 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].C(=O)([O-])[O-].[K+].[K+].[C:17]([C:24](OCC)=[O:25])#[C:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl>C(O)C.O>[CH2:22]([O:21][C:19]([C:18]1[CH:17]=[C:24]([OH:25])[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[Cl:2])[N:10]=1)=[O:20])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 69803Diethyl acetylenedicarboxylateHCID 4432872-Chlorophenylhydrazine hydrochloride

Product 1

HCID 178469350HCID 178469350, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-chlorophenylhydrazine hydrochloride (22.4 g) and potassium carbonate (34.5 g) in ethanol (250 ml) was added diethyl acetylenedicarboxylate (20 ml) and the resulting mixture was heated at reflux for 18 hours. The reaction mixture was cooled, 6 N hydrochloric acid (75 ml) and water (500 ml) were added sequentially. The reaction mixture was extracted with ethyl acetate, the organic layer washed with water, brine, dried (Na2SO4) and concentrated in vacuo. The resulting gum was stirred with isopropyl ether (250 ml) to afford the title compound (I-1a) as a tan solid, (23 g) after filtering and drying in vacuo.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe organic layer washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d502d4977a54d57a7908cc9c9ab63c0
Source dataset
uspto-grants-2007_06
Patent number
US07230024B2

Reaction notes

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