Chlorosuccinimide → 5-Chloro-6-[3-(trifluoromethyl)phenyl]-4-pyridazinamine

HRID 54651Notes

Reaction equation

HRID 54651 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[N:13][CH:12]=[C:11]([NH2:15])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:18]N1C(=O)CCC1=O.CCOC(C)=O.C1CCCCC1>CC#N>[Cl:18][C:10]1[C:11]([NH2:15])=[CH:12][N:13]=[N:14][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 199596756-[3-(Trifluoromethyl)phenyl]-4-pyridazinamineHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 199596635-Chloro-6-[3-(trifluoromethyl)phenyl]-4-pyridazinamineYield 52.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-[3-(Trifluoromethyl)phenyl]-4-pyridazinamine (2.0 g, 0.0084 mole, Compound No. 4) and N-chlorosuccinimide (0.61 g, 0.004 mole) were refluxed under N2 in CH3CN (50 mL) for 1.5 h. After this time no starting material was present by TLC. The mixture was partitioned between EtOAc/water. The organic layer was extracted again with water, dried (MgSO4), filtered and evaporated to give a crude oil. The oil was chromatographed on a Prep-500 using EtOAc/cyclohexane (9:1) to give a crude solid. The solid was recrystal-lized from EtOAc/cyclohexane to give 5-chloro-6-[3-(trifluoromethyl)phenyl]-4-pyridazinamine (0.57 g, 50% yield, Compound No. 35) as a tan solid.

Workup

  1. customThe mixture was partitioned between EtOAc/water
  2. extractionThe organic layer was extracted again with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a crude oil
  7. customThe oil was chromatographed on a Prep-500 using EtOAc/cyclohexane (9:1)
  8. customto give a crude solid

Sources & evidence

ORD record
ord-3e88cd67d4274391af0fbff79444f575
Source dataset
uspto-grants-1997_04
Patent number
US05623072

Reaction notes

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