Hydrochloric Acid → HCID 67287365, compound

HRID 1626493Notes

Reaction equation

HRID 1626493 reaction equation
O=[CH:2][CH:3]([NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:4]=O.Cl.[Cl:16][C:17]1[CH:18]=[C:19]([NH:23][NH2:24])[CH:20]=[CH:21][CH:22]=1.Cl>C(O)C>[Cl:16][C:17]1[CH:18]=[C:19]([N:23]2[CH:4]=[C:3]([NH:6][C:7](=[O:14])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:2]=[N:24]2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 86664397HCID 86664397, compound

Product 1

HCID 67287365HCID 67287365, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(1,3-dioxopropan-2-yl)benzamide (1 g, 5.2 mmol) and (3-chlorophenyl)hydrazine hydrochloride (0.94 g, 5.2 mmol) were mixed with 1N HCl (5 mL), ethanol (40 mL) and concentrated HCl was added (1 mL). The reaction was heated to boiling for 10 minutes and then allowed to cool. The solvent was removed by rotary evaporation. To the resulting residue was added water (20 mL) and dilute ammonium hydroxide (10%) to pH 11. The solids were collected by filtration and washed with water, then dried under vacuum to provide the title compound (1.34 g, 88%).

Workup

  1. additionwas added (1 mL)
  2. temperatureThe reaction was heated
  3. temperatureto cool
  4. customThe solvent was removed by rotary evaporation
  5. additionTo the resulting residue was added water (20 mL) and dilute ammonium hydroxide (10%) to pH 11
  6. filtrationThe solids were collected by filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-03fa6ca9c0304f17a9eb72086426161c
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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