Dimethylamine → HCID 20226927, compound

HRID 1731715Notes

Reaction equation

HRID 1731715 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([CH3:9])[C:7]=1[CH3:8].[CH3:16][NH:17][CH3:18]>I>[CH3:16][N:17]([CH3:18])[C:2]1[N:3]=[N:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([CH3:9])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 20226916HCID 20226916, compound

Product 1

HCID 20226927HCID 20226927, compound

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideCatalyst

Procedure

A 1.5 g sample of 3-chloro-4,5-dimethyl-6-phenylpyridazine is placed in a 6 oz. glass pressure bottle and covered with 15 mL of condensed dimethylamine. To this mixture is added several drops of HI. The bottle is then closed, fitted with a pressure guage and heated for 50 hours at 90°-100° C. and 85-100 psig pressure. The mixture is cooled, excess dimethylamine is evaporated, and the residue partitioned between CH2Cl2 and water. The organic layer is separated and dried over MgSO4. Removal of the drying agent and concentration of the solvent in vacuo leaves a brown solid (1.7 g). The crude solid is boiled in cyclohexane, filtered; the filtrate diluted with hexane and chilled. The product (0.7 g) is isolated as a mustard-colored solid which melts at 86°-89° C.

Workup

  1. customThe bottle is then closed
  2. customfitted with a pressure guage
  3. temperatureheated for 50 hours at 90°-100° C.
  4. temperatureThe mixture is cooled
  5. customexcess dimethylamine is evaporated
  6. customthe residue partitioned between CH2Cl2 and water
  7. customThe organic layer is separated
  8. dry with materialdried over MgSO4
  9. customRemoval of the drying agent and concentration of the solvent in vacuo

Sources & evidence

ORD record
ord-e75203f4247544028b8a4bf1a2aa34c4
Source dataset
uspto-grants-1986_11
Patent number
US04623376

Reaction notes

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