Dimethylamine → HCID 13519316, compound

HRID 1980551Notes

Reaction equation

HRID 1980551 reaction equation
CO[C:3]([C:5]1[N:23]=[C:8]2[CH2:9][N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[C:16]([N:7]2[N:6]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:4].[CH3:24][NH:25][CH3:26]>CO>[CH3:24][N:25]([CH3:26])[C:3]([C:5]1[N:23]=[C:8]2[CH2:9][N:10]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11]3[C:16]([N:7]2[N:6]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:4]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 13519258HCID 13519258, compound

Product 1

HCID 13519316HCID 13519316, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7.00 g (0.023 mol) of the 5-phenyl-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylic acid methyl ester prepared according to Example 1(f) in 300 ml of methanol and 62.6 ml (0.457 mol) of 33% ethanolic dimethylamine solution is heated at 100° in an autoclave for 16 hours. The reaction mixture is then concentrated by evaporation in vacuo and the residue is dissolved in methylene chloride and a mixture of ice and water. The organic phase is washed twice with cold 5% potassium bicarbonate solution and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated by evaporation in vacuo. The amorphous residue crystallises when triturated with 300 ml of ether. After filtration and drying in a high vacuum, there is obtained N,N-dimethyl-5-phenyl-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxamide which sinters from 125° and gradually melts at 150°-165°.

Workup

  1. customprepared
  2. concentrationThe reaction mixture is then concentrated by evaporation in vacuo
  3. dissolutionthe residue is dissolved in methylene chloride
  4. additiona mixture of ice and water
  5. washThe organic phase is washed twice with cold 5% potassium bicarbonate solution and once with saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation in vacuo
  8. customThe amorphous residue crystallises when
  9. customtriturated with 300 ml of ether
  10. filtrationAfter filtration
  11. customdrying in a high vacuum

Sources & evidence

ORD record
ord-ee550b1839ae4b209c284537ad222acc
Source dataset
uspto-grants-1985_04
Patent number
US04510141

Reaction notes

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