Hydrochloric Acid → 3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propylamine

HRID 377718

Reaction equation

HRID 377718 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:24][CH2:25][CH:26]=[C:27]([Cl:29])[Cl:28])[CH:5]=[C:6]([Cl:23])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][N:12]1C(=O)C2=CC=CC=C2C1=O.O.NN.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:24][CH2:25][CH:26]=[C:27]([Cl:29])[Cl:28])[CH:5]=[C:6]([Cl:23])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][NH2:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 185045743,5-Dichloro-4-(3-phthalimidopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

Product 1

HCID 158697443-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propylamineYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction vessel was charged with 4.67 g of crude 3,5-dichloro-4-(3-phthalimidopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.55 g of hydrazine monohydrate and 200 ml of ethanol. After heating under reflux for 2 hours, the reaction mixture was made weak acidic by the addition of concentrated hydrochloric acid, and then further heated under reflux for 1 hours. The deposited solid was collected by filtration, and the filtrate was concentrated. Water was poured into the concentrated, and the mixture was extracted twice with 150 ml of chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography which afforded 2.4 of 3,5-dichloro-4-(3-aminopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (71% yield), nD23.5 1.5672.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 2 hours
  3. temperaturefurther heated
  4. temperatureunder reflux for 1 hours
  5. filtrationThe deposited solid was collected by filtration
  6. concentrationthe filtrate was concentrated
  7. additionWater was poured into the concentrated
  8. extractionthe mixture was extracted twice with 150 ml of chloroform
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated
  12. customto give a crude product

Sources & evidence

ORD record
ord-8d889ed29cec46e1a4beb9b0e019ba19
Source dataset
uspto-grants-2000_02
Patent number
US06028100

Linked notes

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