Ammonium Chloride → HCID 54596448, compound

HRID 2427788Notes

Reaction equation

HRID 2427788 reaction equation
Br[C:2]1[C:3](=[O:18])[N:4]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=2)[N:5]=[CH:6][C:7]=1[O:8][CH3:9].C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[Cl:17][C:12]1[CH:11]=[C:10]([N:4]2[C:3](=[O:18])[CH:2]=[C:7]([O:8][CH3:9])[CH:6]=[N:5]2)[CH:15]=[C:14]([Cl:16])[CH:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 54596450HCID 54596450, compoundHCID 178418339Butyllithium2×

Product 1

HCID 54596448HCID 54596448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-2-(3,5-dichlorophenyl)-5-methoxypyridazin-3-one (2.5 g, 0.0071 moles) was dissolved in THF (250 ml) and cooled to −50° under nitrogen. 1.6M n-Butyl lithium (6.7 ml, 0.011 moles) was added dropwise with stirring. Allowed to warm to −20° over 1 hour. Added 1 equivalent of 1.6M n-Butyl lithium (4.4 ml, 0.0071 moles) dropwise. Stirred at −20° for 30 minutes. Poured into ammonium chloride solution and stirred for 15 minutes. Extracted with EtOAc (×2) and washed with water. Dried over anhydrous magnesium sulphate, filtered and evaporated to give a brown solid. (3.0 g) Purified using MPLC (silica, eluted with dichloromethane: EtOAc 9:1) to give a yellow solid. (0.25 g, 13%) Not pure used directly in the next reaction.

Workup

  1. temperaturecooled to −50° under nitrogen
  2. temperatureAllowed to warm to −20° over 1 hour
  3. stirringStirred at −20° for 30 minutes
  4. stirringstirred for 15 minutes
  5. extractionExtracted with EtOAc (×2)
  6. washwashed with water
  7. dry with materialDried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customto give a brown solid
  11. custom(3.0 g) Purified
  12. washMPLC (silica, eluted with dichloromethane: EtOAc 9:1)
  13. customto give a yellow solid
  14. custom(0.25 g, 13%) Not pure used directly in the next reaction

Sources & evidence

ORD record
ord-bc6330eb51ce4106867bde1c09e5ffa0
Source dataset
uspto-grants-2011_06
Patent number
US07968711B2

Reaction notes

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