Dichloroacetic Acid → 7-t-Butyl-6-chloro-3-dichloromethyl-1,2,4-triazolo[4,3-b]pyridazine

HRID 378840Notes

Reaction equation

HRID 378840 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([NH:11][NH2:12])[N:8]=[N:7][C:6]=1[Cl:13])([CH3:4])([CH3:3])[CH3:2].[Cl:14][CH:15]([Cl:19])[C:16](O)=O>C1(C)C=CC=CC=1>[C:1]([C:5]1[C:6]([Cl:13])=[N:7][N:8]2[C:16]([CH:15]([Cl:19])[Cl:14])=[N:12][N:11]=[C:9]2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6597Dichloroacetic AcidHCID 229878864-(tert-Butyl)-3-chloro-6-hydrazinylpyridazine

Product 1

HCID 184306857-t-Butyl-6-chloro-3-dichloromethyl-1,2,4-triazolo[4,3-b]pyridazineYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-t-Butyl-3-chloro-6-hydrazinopyridazine (9.5 g, 48 mmol) and dichloroacetic acid (20 ml) were heated in toluene (130 ml) under Dean Stark conditions for 2.5 hours. The toluene was removed and the residue was poured into water to precipitate the product as a brown solid. The product was purified by chromotography on silica gel using 10% ethyl acetate/dichloromethane as eluant to yield a yellow solid (10.4 g, 74%), 1H NMR (250 MHz, CDCl3) δ 1.59 (9H, s, t-Bu), 6.01 (1H, s, CM), 8.37 (1H, s, ArH); MS (ES+) m/e 293 [MH]+.

Workup

  1. customThe toluene was removed
  2. additionthe residue was poured into water
  3. customto precipitate the product as a brown solid
  4. customThe product was purified by chromotography on silica gel using 10% ethyl acetate/dichloromethane as eluant

Sources & evidence

ORD record
ord-c8516d8c863f45d6b8979983524f75fe
Source dataset
uspto-grants-2001_10
Patent number
US06297235B1

Reaction notes

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