4-Ethoxyaniline → HCID 86611716, compound

HRID 2239826Notes

Reaction equation

HRID 2239826 reaction equation
O[C:2]1[C:3]([Cl:12])=[C:4]([Cl:11])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.CCOC1C=CC(N)=CC=1.O=P(Cl)(Cl)[Cl:25]>C(Cl)Cl>[Cl:25][C:2]1[C:3]([Cl:12])=[C:4]([Cl:11])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 90764-EthoxyanilineHCID 24813Phosphorus oxychlorideHCID 178518858HCID 178518858, compound

Product 1

HCID 86611716HCID 86611716, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

6-Hydroxy-7,8-dichloroimidazo[1,2-b]pyridazine (0.1 g, 0.5 mmol) from 1c was added to POCl3 (0.4 mL, 1.4 M) in a 1 dram vial. The mixture was heated to 120° C. for 2 days. Upon cooling CH2Cl2 was added and the mixture was poured onto ice water. The layers were separated and the aqueous layer was extracted with CH2Cl2 (15 mL). The organic layers were combined and washed with H2O (5 mL), followed by brine (5 mL). The solution was dried over Na2SO4 and concentrated in vacuo to give 6,7,8-trichloroimidazo[1,2-b]pyridazine as a tan solid (0.04 g, 37%).

Workup

  1. additionwas added
  2. additionthe mixture was poured onto ice water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (15 mL)
  5. washwashed with H2O (5 mL)
  6. dry with materialThe solution was dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed5a5656293a4f5796196b82d4fb4849
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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