Pyridine → 3-(3-Methyl-1,2,4-thiadiazol-5-yl)-6-[[4-[3-(trifluoromethyl)phenoxy]butyl]thio]pyridazine

HRID 394490Notes

Reaction equation

HRID 394490 reaction equation
C[N:2](C)[C:3](=[N:5][C:6]([C:8]1[N:9]=[N:10][C:11]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[CH:12][CH:13]=1)=[S:7])[CH3:4].N1C=CC=CC=1.NOS(O)(=O)=O>C(O)C.CO>[CH3:4][C:3]1[N:5]=[C:6]([C:8]2[N:9]=[N:10][C:11]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[CH:12][CH:13]=2)[S:7][N:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 76284hydroxylamine-O-sulfonic acidHCID 18176643HCID 18176643, compound

Product 1

HCID 181766373-(3-Methyl-1,2,4-thiadiazol-5-yl)-6-[[4-[3-(trifluoromethyl)phenoxy]butyl]thio]pyridazineYield 26.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of intermediate 13 (0.009 mol) and pyridine (0.02 mol) in ethanol (80 ml) was stirred. A mixture of hydroxylamine-O-sulfonic acid (0.01 mol) in methanol (20 ml) was added. The mixture was stirred overnight. The solvent was evaporated. The residue was taken up in DCM. The organic solution was washed with a diluted NaOH solution and with water, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent:DCM). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanol. The precipitate was filtered off and dried, yielding 1 g (26%) of 3-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[[4-[3-(trifluoromethyl)phenoxy]butyl]thio]pyridazine (compound 94).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred overnight
  3. customThe solvent was evaporated
  4. washThe organic solution was washed with a diluted NaOH solution and with water
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent:DCM)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from 2-propanol
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-81ed27c031b245ae961b0eff76a714a9
Source dataset
uspto-grants-2003_08
Patent number
US06602873B2

Reaction notes

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