Sodium Iodide → 1-(4-Chloro-2-(2-chlorobenzoyl)phenyl)-5-(morpholinomethyl)-1H-1,2,4-triazole-3-carboxylic acid monohydrochloride

HRID 1706988Notes

Reaction equation

HRID 1706988 reaction equation
[I-].[Na+].[Cl:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[C:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[N:15]1[C:19]([CH2:20]Cl)=[N:18][C:17]([C:22]([OH:24])=[O:23])=[N:16]1)=[O:7].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C(O)C>[ClH:3].[Cl:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[C:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[N:15]1[C:19]([CH2:20][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[N:18][C:17]([C:22]([OH:24])=[O:23])=[N:16]1)=[O:7]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 13255884HCID 13255884, compound

Product 1

HCID 64556531-(4-Chloro-2-(2-chlorobenzoyl)phenyl)-5-(morpholinomethyl)-1H-1,2,4-triazole-3-carboxylic acid monohydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.10 g of sodium iodide is added to a mixture of 9.3 g (0.0226 mole) of 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxylic acid (see German `Offenlegungsschrift` No. 2,159,527, page 32) and 9.5 g (0.11 mole) of morpholine in 100 ml of ethanol, and the whole is reflux for 2 hours. The reaction mixture is thereupon concentrated in vacuo; the residue is dissolved in water, and 2N hydrochloric acid is added until an acid reaction to Congo red is obtained. The precipitated hydrochloride of the reaction product is extracted twice with 100 ml of methylene chloride each time. After washing with saturated sodium chloride solution, drying over sodium sulphate and concentration by evaporation, the organic extracts yield 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(morpholinomethyl)-1H-1,2,4- triazole-3-carboxylic acid hydrochloride in the form of an amorphous yellow foam, which is used directly for the next step.

Workup

  1. concentrationThe reaction mixture is thereupon concentrated in vacuo
  2. dissolutionthe residue is dissolved in water
  3. addition2N hydrochloric acid is added until an acid reaction to Congo red
  4. customis obtained
  5. extractionThe precipitated hydrochloride of the reaction product is extracted twice with 100 ml of methylene chloride each time
  6. washAfter washing with saturated sodium chloride solution
  7. dry with materialdrying over sodium sulphate and concentration by evaporation

Sources & evidence

ORD record
ord-3e78f23f7211436a90719e89d9581e3e
Source dataset
uspto-grants-1980_06
Patent number
US04209516

Reaction notes

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