Dimethylamine → HCID 53665129, compound

HRID 1706993Notes

Reaction equation

HRID 1706993 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]=[C:8]([CH2:10]I)[N:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:6]=1)=[O:4].[CH3:28][NH:29][CH3:30]>CO>[CH3:1][O:2][C:3]([C:5]1[N:9]=[C:8]([CH2:10][N:29]([CH3:30])[CH3:28])[N:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 54482160HCID 54482160, compound

Product 1

HCID 53665129HCID 53665129, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 12.90 g (0.025 mole) of 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(iodomethyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester [see Example 13 (b)] and 11 ml of 33% ethanolic dimethylamine solution in 250 ml of methanol is stirred for 7 hours at room temperature. The reaction solution is thereupon concentrated in vacuo; water is added to the residue and the whole is extracted twice with methylene chloride. The organic phase is washed twice with water and once with saturated sodium chloride solution; it is dried over sodium sulphate and concentrated in vacuo to dryness. The amorphous residue is dissolved in 130 ml of ether; the solution is allowed to stand and the reaction product then crystallises out. It is filtered off with suction and washed with ether. After drying there is obtained 1-[2-(o-chlorobenzoyl)-4-chlorophenyl)-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxylic acid methyl ester, m.p. 131°-134°.

Workup

  1. concentrationThe reaction solution is thereupon concentrated in vacuo
  2. additionwater is added to the residue
  3. extractionthe whole is extracted twice with methylene chloride
  4. washThe organic phase is washed twice with water and once with saturated sodium chloride solution
  5. dry with materialit is dried over sodium sulphate
  6. concentrationconcentrated in vacuo to dryness
  7. dissolutionThe amorphous residue is dissolved in 130 ml of ether
  8. customthe reaction product then crystallises out
  9. filtrationIt is filtered off with suction
  10. washwashed with ether
  11. customAfter drying there

Sources & evidence

ORD record
ord-fc636cd5e16f470e8e7bbfbc92a64f22
Source dataset
uspto-grants-1980_06
Patent number
US04209516

Reaction notes

Loading…