Hydrochloric Acid → HCID 22006731, compound

HRID 377720Notes

Reaction equation

HRID 377720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:25][CH2:26][CH:27]=[C:28]([Cl:30])[Cl:29])[CH:5]=[C:6]([Cl:24])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1C(=O)C2=CC=CC=C2C1=O.O.NN.Cl.[OH-].[K+]>C(O)C.C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:25][CH2:26][CH:27]=[C:28]([Cl:30])[Cl:29])[CH:5]=[C:6]([Cl:24])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 22006866HCID 22006866, compound

Product 1

HCID 22006731HCID 22006731, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 14.5 g of 3,5-dichloro-4-(4-phthalimidobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 1.73 ml of hydrazine monohydrate and 100 ml of ethanol was heated under reflux for 4 hours. The reaction mixture was made weak acidic by the addition of concentrated hydrochloric acid and further heated under reflux for 1 hour. The temperature of the reaction mixture was decreased to room temperature, after which the deposited solid was collected by filtration and the filtrate was concentrated to give a residue. To the residue was added a solution of 2.1 g of potassium hydroxide dissolved in 100 ml of ethanol, after which the deposited solid was collected by filtration and the filtrate was concentrated to give a residue. To the residue was added 100 ml of diethyl ether for dissolution, and the solution was dried over anhydrous magnesium sulfate and then concentrated, which afforded 7.51 g of 3,5-dichloro-4-(4-aminobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (71% yield), nD23.5 1.5672.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperaturefurther heated
  4. temperatureunder reflux for 1 hour
  5. customwas decreased to room temperature
  6. filtrationafter which the deposited solid was collected by filtration
  7. concentrationthe filtrate was concentrated
  8. customto give a residue
  9. filtrationafter which the deposited solid was collected by filtration
  10. concentrationthe filtrate was concentrated
  11. customto give a residue
  12. dissolutionfor dissolution
  13. dry with materialthe solution was dried over anhydrous magnesium sulfate
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-ce3eaaee0370488688e0305f4dd6cd5a
Source dataset
uspto-grants-2000_02
Patent number
US06028100

Reaction notes

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