Diphosgene → HCID 15595663, compound

HRID 35621Notes

Reaction equation

HRID 35621 reaction equation
[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[CH:18]([N:21]([CH:24](C)C)[CH2:22]C)(C)C.ClC(OC(Cl)(Cl)Cl)=[O:29].Cl.CNC.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:18][N:21]([CH3:24])[C:22]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2]([CH3:1])=[N:3][N:4]=3)[N:7]=2)[CH:12]=1)=[O:29]

Participants

7

Reactant 5

HCID 10426DiphosgeneHCID 10473Dimethylamine, hydrochlorideHCID 81531Diisopropylethylamine2×HCID 516892Sodium BicarbonateHCID 127268683-Methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 15595663HCID 15595663, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a soluton of 1.9 g of 3-methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine and 1.6 of diisopropylethylamine in dichloromethane was added 1.67 g of trichloromethyl chloroformate. This mixture was stirred for 1 hour, then two equivalents of dimethylamine hydrochloride were added. Diisopropylethylamine was added until solution was complete then the mixture was stirred for 1 hour, poured into saturated aqueous sodium bicarbonate and extracted with dichloromethane. The extracts were combined, dried and the solvent removed. The residue was chromatographed on a 200 g silica gel column using dichloromethane:methanol (95:5) as eluent. The active fractions were combined, evaporated and the solid recrystallized from dichloromethane-methanol-hexane, giving 1.33 g of the desired product as pale yellow crystals, mp 237°-239° C.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionextracted with dichloromethane
  3. customdried
  4. customthe solvent removed
  5. customThe residue was chromatographed on a 200 g silica gel column
  6. customevaporated
  7. customthe solid recrystallized from dichloromethane-methanol-hexane

Sources & evidence

ORD record
ord-652963b9c25a4c25b553f6a769f4f916
Source dataset
uspto-grants-1988_08
Patent number
US04767765

Reaction notes

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