Water → 5-chloro-2-[3-(2-chloroacetamidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-benzophenone

HRID 25939Notes

Reaction equation

HRID 25939 reaction equation
Br.Br.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:18]2[C:22]([CH3:23])=[N:21][N:20]=[C:19]2[CH2:24][NH2:25])=[C:8]([CH:17]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].[Cl:26][CH2:27][C:28](Cl)=[O:29].O.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:18]2[C:22]([CH3:23])=[N:21][N:20]=[C:19]2[CH2:24][NH:25][C:28](=[O:29])[CH2:27][Cl:26])=[C:8]([CH:17]=1)[C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:10]

Participants

7

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 213257365-chloro-2-(3-aminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone dihydrobromide

Product 1

HCID 155678665-chloro-2-[3-(2-chloroacetamidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-benzophenoneYield 84.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-2-(3-aminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone dihydrobromide (0.5 g) in dimethylformamide (3 ml), chloroacetyl chloride (0.2 g) is dropwise added under ice cooling, and the resultant mixture is stirred. The reaction mixture is allowed to stand at room temperature overnight, mixed with water (3 ml), neutralized with aqueous sodium bicarbonate and shaken with methylene chloride. The methylene chloride layer is washed with water and saturated aqueous saline solution in order, dried over sodium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is recrystallized from ethyl acetate/n-hexane to give 5-chloro-2-[3-(2-chloroacetamidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-benzophenone (0.35 g) as crystals melting at 140° to 141° C.

Workup

  1. washThe methylene chloride layer is washed with water and saturated aqueous saline solution in order
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customto remove the solvent
  5. customThe residue is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-aae191a3852d4aac82b2afa6a514a58d
Source dataset
uspto-grants-1979_04
Patent number
US04147700

Reaction notes

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