Toluene → HCID 57264165, compound

HRID 359786Notes

Reaction equation

HRID 359786 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH2:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[CH:10]=[CH2:11].[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH3:25]N1CCCC1=O.[C:32]1([CH3:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O>[CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][C:2]1[N:3]=[N:4][C:5]([O:22][C:19]2[CH:25]=[CH:33][CH:34]=[CH:35][C:36]=2[CH:37]=[CH:32][CH3:38])=[CH:6][CH:7]=1)=[CH:10][CH3:11]

Participants

7

Reactant 5

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 156242-AllylphenolHCID 673313,6-Dichloropyridazine

Product 1

HCID 57264165HCID 57264165, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 149 g of 3,6-dichloropyridazine, 268.4 g of 2-allylphenol, 152 g of potassium carbonate, 400 ml of N-methylpyrrolidone and 900 ml of toluene was heated at 140° C. for 30 hours, the resulting water of reaction being distilled off azeotropically. Working up similarly to Example la) gave 317 g (92%) of a partially crystalline product, which consisted of an isomer mixture of allyl-containing and propenyl-containing products. After the addition of methanol and filtration, 140 g of pure 3,6-bis-(2-propenylphenoxy)-pyridazine were obtained as colorless crystals of melting point 165°-168° C.; 1H-NMR: 1.80 (d, CH ), 5.70-5.90 (m, small amount of cis-isomer), 6.20-6.50 (m, 4H, olef.) 7.0-7.7 (m, 1OH, arom.).

Workup

  1. distillationbeing distilled off azeotropically
  2. additionconsisted of an isomer mixture of allyl-
  3. additioncontaining
  4. additionpropenyl-containing products
  5. additionAfter the addition of methanol and filtration

Sources & evidence

ORD record
ord-baf9f7fceb784c7bb6cb377d847434f4
Source dataset
uspto-grants-1991_03
Patent number
US05003017

Reaction notes

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