Hydrochloric Acid → HCID 85769592, compound

HRID 1580477Notes

Reaction equation

HRID 1580477 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N:9](C(=O)C1C=CC=CC=1)[NH2:10].P(Cl)(Cl)(Cl)(Cl)Cl.Cl.[C:26]1(O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:33](Cl)(Cl)(Cl)[Cl:34]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][N:10]=[C:33]([Cl:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 5943Carbon Tetrachloride2×HCID 24819Phosphorus pentachlorideHCID 54255782HCID 54255782, compound

Product 1

HCID 85769592HCID 85769592, compound

Procedure

A quantity (16.87 g., 0.06 mole) benzoic acid (2,5-dichlorophenyl)hydrazide (Preparation II, above) was added to a solution of 12.50 g. (0.06 mole) phosphorous pentachloride in 50 ml. carbon tetrachloride, and the resulting suspension was allowed to react at 25°C. until evolution of hydrogen chloride gas slowed. The reaction mixture was then heated at the reflux temperature for 15 minutes, chilled in ice, and 17.8 g. (0.19 mole) phenol in 75 ml. carbon tetrachloride was added. After the reaction was completed, the carbon tetrachloride was removed by evaporation under reduced pressure at 30° to 32° C. The resulting suspension was filtered, and the filter cake was washed with 50 ml. cold methanol. Two recrystallizations from Skellysolve B gave benzoyl chloride (2,5-dichlorophenyl)hydrazone melting at 84.5° to 86° C.

Workup

  1. temperatureThe reaction mixture was then heated at the reflux temperature for 15 minutes
  2. temperaturechilled in ice
  3. customthe carbon tetrachloride was removed by evaporation under reduced pressure at 30° to 32° C
  4. filtrationThe resulting suspension was filtered
  5. washthe filter cake was washed with 50 ml
  6. customTwo recrystallizations from Skellysolve B

Sources & evidence

ORD record
ord-13959350288b4aefb8a6a4c0d8746024
Source dataset
uspto-grants-1976_01
Patent number
US03932661

Reaction notes

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