Hydrochloric Acid → HCID 86732895, compound

HRID 597669Notes

Reaction equation

HRID 597669 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[C:7]1([NH:13][NH:14][C:15](=O)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22][CH3:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[ClH:25].C1(O)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:7]1([NH:13][N:14]=[C:15]([Cl:2])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:25])[C:17]=2[S:22][CH3:23])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 24819Phosphorus pentachlorideHCID 54253349HCID 54253349, compound

Product 1

HCID 86732895HCID 86732895, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A mixture consisting of 21.9 g. (0.105 mole) phosphorus pentachloride, 150 ml. of carbon tetrachloride, and 25.83 g. (0.100 mole) o-(methylthio)benzoic acid 2-phenylhydrazide (prepared in Part A above) was heated at the reflux temperature until evolution of hydrogen chloride ceased. The reaction mixture was chilled in an ice-bath, and a suspension of 31.5 g, (0.335 mole) phenol in 50 ml. carbon tetrachloride was added. After removing the carbon tetrachloride by evaporation under reduced pressure, the resulting triphenylphosphate solution of the desired product was poured through a column of silica gel. Elution was effected with a mixture consisting of 1 part benzene and 1 part Skellysolve B. After removing the solvents from the eluate by evaporation under reduced pressure, 2.0 g. of residue was obtained. Recrystallization from petroleum ether gave an o-(methylthio)-chlorobenzoyl chloride phenylhydrazone having a melting point at 65° to 66.5° C.

Workup

  1. temperatureThe reaction mixture was chilled in an ice-bath
  2. customAfter removing the carbon tetrachloride
  3. customby evaporation under reduced pressure
  4. additionthe resulting triphenylphosphate solution of the desired product was poured through a column of silica gel
  5. washElution
  6. customAfter removing the solvents from the
  7. customeluate by evaporation under reduced pressure, 2.0 g
  8. customof residue was obtained
  9. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-89d98ec38f514543aca7291010989af3
Source dataset
uspto-grants-1977_03
Patent number
US04014932

Reaction notes

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