Formic Acid → HCID 21455954, compound

HRID 1729877Notes

Reaction equation

HRID 1729877 reaction equation
[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16]([C:19]([O:21]CC)=[O:20])[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[N:6][CH:5]=1)([O-:3])=[O:2].C(O)=O.CS(O)(=O)=O>O>[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16]([C:19]([OH:21])=[O:20])[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 284Formic AcidHCID 6395Methanesulfonic AcidHCID 21455995HCID 21455995, compound

Product 1

HCID 21455954HCID 21455954, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.8 g. 3-(5-nitro-1-methyl-2-imidazolyl)-6-carbethoxy-s-triazolo[4,3-b]pyridazine were heated under reflux with 18.3 ml. 90 percent aqueous formic acid and 2.75 ml. methane-sulfonic acid for 3 hours at a bath temperature of 130° C. 80 ml. water were then added thereto and the precipitated crystals were filtered off with suction, after having stood for 1 hour, and washed with water. There were thus obtained 4.85 g. 3-(5-nitro-1-methyl-2-imidazolyl)-6-carboxy-s-triazolo[4,3-b]pyridazine, which has a melting point of 257° - 260° C. 1 g. of the product was recrystallized from 15 ml. dioxan with the addition of charcoal, to give 0.6 g. of pure product which melts, with foaming up, at 260° - 262° C.

Workup

  1. temperatureunder reflux with 18.3 ml
  2. filtrationthe precipitated crystals were filtered off with suction
  3. washwashed with water
  4. customof the product was recrystallized from 15 ml
  5. additiondioxan with the addition of charcoal
  6. customto give 0.6 g
  7. customwith foaming up, at 260° - 262° C.

Sources & evidence

ORD record
ord-0b2e715cb0624280912ff1667ea20373
Source dataset
uspto-grants-1976_11
Patent number
US03989832

Reaction notes

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