Chlorosuccinimide → HCID 22591558, compound

HRID 22748Notes

Reaction equation

HRID 22748 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[N:5][C:6]([S:9][C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=1.[Cl:19]N1C(=O)CCC1=O>CO>[CH3:1][O:2][C:3]1[N:4]=[N:5][C:6]([S:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[Cl:19])=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 120717643-Methoxy-6-(indole-2-sulfenyl)-pyridazine

Product 1

HCID 22591558HCID 22591558, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-methoxy-6-(indole-2-sulfenyl)-pyridazine) (2.92 mmol, 750 mg), N-chloro-succinimide (2.92 mmol, 390 mg) and methanol (15 mL) was stirred overnight at room temperature. Excess methanol was removed and the residue was extracted with EtOAc (3×10 mL). The EtOAc extract was collected, dried, filtered and evaporated to dryness to obtain a residue, which was purified by silica gel chromatography (eluent:hexanes:EtOAc::19:5) to yield 3-methoxy-6-(3-chloro-indole-2-sulfenyl)-pyridazine (40%, 338 mg).

Workup

  1. customExcess methanol was removed
  2. extractionthe residue was extracted with EtOAc (3×10 mL)
  3. extractionThe EtOAc extract
  4. customwas collected
  5. customdried
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto obtain a residue, which
  9. customwas purified by silica gel chromatography (eluent:hexanes:EtOAc::19:5)

Sources & evidence

ORD record
ord-573ba61d162e49dd86ea5bb52ca15369
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Reaction notes

Loading…