Dimethylamine → HCID 21455928, compound

HRID 1729863Notes

Reaction equation

HRID 1729863 reaction equation
[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16](Cl)[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[N:6][CH:5]=1)([O-:3])=[O:2].O1CCOCC1.[CH3:26][NH:27][CH3:28]>CO>[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16]([N:27]([CH3:28])[CH3:26])[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[N:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 312751,4-DioxaneHCID 21455925HCID 21455925, compound

Product 1

HCID 21455928HCID 21455928, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1.4 g. 3-(5-nitro-1-methyl-2-imidazolyl)-6-chloro-s-triazolo [4,3-b]pyridazine was suspended in 14 ml. of a mixture of dioxan and methanol (1:1), 6.7 ml. 30percent methanolic dimethylamine solution were added thereto, the reaction mixture was stirred for 1 hour at 60° C., then cooled in an ice bath, the product was filtered off with suction, washed with a mixture of dioxan and methanol (1:1) and then with ether and the product thus obtained (0.66 g.) recrystallized from 15 ml. dioxan-dimethylformamide (9:1), with the addition of charcoal, 0.35 g. of intense yellow crystals of the desired 3-(5-nitro-1-methyl-2-imidazolyl)-6-dimethylamino-s-triazolo [4,3-b]pyridazine thereby being obtained. It has a melting point of 233° -236° C.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationthe product was filtered off with suction
  3. washwashed with a mixture of dioxan and methanol (1:1)
  4. customwith ether and the product thus obtained (0.66 g.)
  5. customrecrystallized from 15 ml
  6. additiondioxan-dimethylformamide (9:1), with the addition of charcoal, 0.35 g

Sources & evidence

ORD record
ord-7ca9682ce6f04ddcae6f8b4aa1a68b40
Source dataset
uspto-grants-1976_11
Patent number
US03989832

Reaction notes

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