Ethyl orthoformate → Ethyl (3,5-dichloropyridazin-4-yl)imidoformate

HRID 1846027Notes

Reaction equation

HRID 1846027 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1N.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+:21]1[CH:26]=CC=CC=1.C(OCC)(OCC)[O:28][CH2:29][CH3:30]>>[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[C:26](=[NH:21])[O:28][CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 31214Ethyl orthoformateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 64032013,5-Dichloro-1,4-dihydropyridazin-4-imine

Product 1

HCID 86723250Ethyl (3,5-dichloropyridazin-4-yl)imidoformateYield 60%

Procedure

To a stirred suspension of 3,5-dichloro-4-aminopyridazine (5 g, 31 mmol) in triethyl orthoformate (205 mL) was added pyridinium para-toluenesulfonate (387 mg, 1.5 mmol) and the resultant solution was heated at 100° C. for 16 hours. The reaction mixture was cooled to room temperature then evaporated in vacuo and the crude residue was purified by silica gel column chromatography eluting with hexane:EtOAc (80:20) to afford the title compound as a light brown oil in 60% yield, 4 g.

Workup

  1. customthen evaporated in vacuo
  2. customthe crude residue was purified by silica gel column chromatography
  3. washeluting with hexane:EtOAc (80:20)

Sources & evidence

ORD record
ord-86ad46f5e07143a6b5022896ce376654
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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