Hydrochloric Acid → HCID 67693473, compound

HRID 1417308Notes

Reaction equation

HRID 1417308 reaction equation
[N:1]1([C:6]2[CH:27]=[CH:26][C:9]([O:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.NN.Cl>C(O)C>[N:1]1([C:6]2[CH:27]=[CH:26][C:9]([O:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][NH2:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 67693623(E)-2-[4-[4-(1H-Imidazol-1-yl)phenoxy]-2-buten-1-yl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 67693473HCID 67693473, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 26.2 g of (E)2-[4-[4-(1H-imidazol-1-yl)phenoxy]-2-buten-1-yl]-1H-isoindole-1,3(2H)-dione (Example 30) in 1 liter of ethanol is treated with 5 ml of anhydrous hydrazine, and the mixture stirred at reflux for 18 hours. To the reaction mixture is added 25 ml of concentrated HCl and the mixture cooled to room temperature. The precipitate is collected and washed with 2 portions of 300 ml of water. The filtrate and aqueous washes are combined and taken to dryness in vacuo. The solid is treated with 25 ml of 10N NaOH, the mixture saturated with solid K2CO3, and then extracted with 500 ml of dichloro-methane. Removal of the dichloromethane in vacuo leaves a viscous oil that solidifies at room temperature. A portion is purified by recrystallization from hexane, and dried; m.p. 81°-83° C.; yield, 0.5 g.

Workup

  1. temperatureat reflux for 18 hours
  2. customThe precipitate is collected
  3. washwashed with 2 portions of 300 ml of water
  4. additionThe solid is treated with 25 ml of 10N NaOH
  5. extractionthe mixture saturated with solid K2CO3, and then extracted with 500 ml of dichloro-methane
  6. customRemoval of the dichloromethane in vacuo
  7. customleaves a viscous oil
  8. customthat solidifies at room temperature
  9. customA portion is purified by recrystallization from hexane
  10. customdried
  11. customyield

Sources & evidence

ORD record
ord-aa2591458e9248a9b2c06e8ee287100a
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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