Dimethylamine → HCID 56626169, compound

HRID 2166499Notes

Reaction equation

HRID 2166499 reaction equation
[CH3:1][NH:2][CH3:3].C(O)(C)C.[NH2:8][N:9]1[C:14](=[O:15])[CH:13]([F:16])[N:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[C:10]1SC>C(O)(=O)C>[NH2:8][N:9]1[C:14](=[O:15])[CH:13]([F:16])[N:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[C:10]1[N:2]([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 3776IsopropanolHCID 70401879HCID 70401879, compound

Product 1

HCID 56626169HCID 56626169, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

13.6 g (0.3 mole) of dimethylamine were introduced into a mixture of 350 ml of isopropanol and 12 g of glacial acetic acid, while cooling with ice. 21.8 g (0.1 mole) of 4-amino-6-fluoro-tert.-butyl-3-methylthio-1,2,4-triazin-5-one (obtained as described in Example 2) were then added to this reaction solution. The mixture was allowed to warm to room temperature and was then heated under reflux for 15 hours. Thereafter, the reaction mixture was concentrated and the oily residue was stirred into water. The mixture was extracted with methylene chloride and the extract was dried over sodium sulphate and concentrated. The oily residue was taken up in diisopropyl ether, seed crystals were added and the solid which crystallized out was filtered off and dried. 15.9 g (69% of theory) of 4-amino-3-dimethylamino-6-fluoro-tert.-butyl-1,2,4-triazin-5-one of melting point 86°-87° C. were obtained.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewas then heated
  3. temperatureunder reflux for 15 hours
  4. concentrationThereafter, the reaction mixture was concentrated
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialthe extract was dried over sodium sulphate
  7. concentrationconcentrated
  8. additionseed crystals were added
  9. customthe solid which crystallized out
  10. filtrationwas filtered off
  11. customdried

Sources & evidence

ORD record
ord-0b63bdf2ca3b47b292028cf3c677f0ec
Source dataset
uspto-grants-1983_06
Patent number
US04386953

Reaction notes

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