Hydrochloric Acid → HCID 178469350, compound

HRID 857468Notes

Reaction equation

HRID 857468 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-baf7876efa274d54a6fcd1cdedc080f4
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

Loading…