Dimethylamine → HCID 20333039, compound

HRID 1706990Notes

Reaction equation

HRID 1706990 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[N:19]1[C:23]([CH2:24]Cl)=[N:22][C:21]([C:26]([NH2:28])=[O:27])=[N:20]1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[I-].[Na+]>CO>[ClH:18].[C:4]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[N:19]1[C:23]([CH2:24][N:2]([CH3:3])[CH3:1])=[N:22][C:21]([C:26]([NH2:28])=[O:27])=[N:20]1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 13255888HCID 13255888, compound

Product 1

HCID 20333039HCID 20333039, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.0 ml of 33% ethanolic dimethylamine solution is added to a mixture of 3.75 g (0.01 mole) of 1-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxamide and 0.15 g of sodium iodide in 70 ml of methanol, and the whole is refluxed for 4 hours with stirring. The reaction mixture is subsequently concentrated in vacuo. Water and saturated sodium carbonate solution are added until the pH-value has reached 10, and extraction is performed twice with ethyl acetate. The organic phase is washed twice with water and once with saturated sodium chloride solution; it is then dried over magnesium sulphate and filtered. To the filtrate there is added ethereal hydrogen chloride solution until the pH-value has reached 3. The product precipitating in crystalline form is filtered off with suction and washed with ethyl acetate and ether. After drying in vacuum, there is obtained 1-(2-benzoyl-4-chlorophenyl)-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide-hydrochloride, m.p. 250° with decomposition.

Workup

  1. temperaturethe whole is refluxed for 4 hours
  2. concentrationThe reaction mixture is subsequently concentrated in vacuo
  3. additionWater and saturated sodium carbonate solution are added until the pH-value
  4. extraction10, and extraction
  5. washThe organic phase is washed twice with water and once with saturated sodium chloride solution
  6. dry with materialit is then dried over magnesium sulphate
  7. filtrationfiltered
  8. additionTo the filtrate there is added ethereal hydrogen chloride solution until the pH-value
  9. customThe product precipitating in crystalline form
  10. filtrationis filtered off with suction
  11. washwashed with ethyl acetate and ether
  12. customAfter drying in vacuum

Sources & evidence

ORD record
ord-82fd81521f7542daae7b57117d45f3f8
Source dataset
uspto-grants-1980_06
Patent number
US04209516

Reaction notes

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