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

HRID 323675

反応式

HRID 323675 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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 I 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.

後処理

  1. temperatureAfter heating
  2. temperatureunder reflux for 2 hours
  3. temperaturefurther heated
  4. temperatureunder reflux for I 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

出典と根拠

ORDレコード
ord-e5fa4c1109f74586bea5ab9723d50ae2
出典データセット
uspto-grants-2001_04
特許番号
US06214835B1

関連ノート

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