Diethyl Ether → 5-chloro-2-(3-glycylaminomethyl-4H-1,2,4-triazol-4-yl)-benzophenone

HRID 614049Notes

Reaction equation

HRID 614049 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[CH:20]=[N:19][N:18]=[C:17]2[CH2:21][NH:22][C:23](=[O:36])[CH2:24][NH:25]C(OCC2C=CC=CC=2)=O)=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].CCOCC>C1(OC)C=CC=CC=1.Br.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[CH:20]=[N:19][N:18]=[C:17]2[CH2:21][NH:22][C:23](=[O:36])[CH2:24][NH2:25])=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 213256755-chloro-2-[3-(N-carbobenzoxyglycyl)aminomethyl-4H-1,2,4-triazol-4-yl]-benzophenone

Product 1

HCID 155678795-chloro-2-(3-glycylaminomethyl-4H-1,2,4-triazol-4-yl)-benzophenoneYield 25.3%

Reagents, catalysts & solvents 2

HCID 7519AnisoleSolventHCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

To a solution of 5-chloro-2-[3-(N-carbobenzoxyglycyl)aminomethyl-4H-1,2,4-triazol-4-yl]-benzophenone (2.1 g) in anisole (4 ml), 30% hydrogen bromide-acetic acid is added. The resultant mixture is stirred for 1 hour and mixed with ether. The precipitate is filtered, washed with ether and dissolved in methylene chloride (20 ml). The methylene chloride layer is washed with saturated aqueous sodium bicarbonate, water and saturated aqueous saline solution in order, dried over sodium sulfate and evaporated under reduced pressure to remove the solvent. The residue is chromatographed on a column of silica gel, which is eluted with methanol to give 5-chloro-2-(3-glycylaminomethyl-4H-1,2,4-triazol-4-yl)-benzophenone as a colorless oil (0.39 g).

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with ether
  3. dissolutiondissolved in methylene chloride (20 ml)
  4. washThe methylene chloride layer is washed with saturated aqueous sodium bicarbonate, water and saturated aqueous saline solution in order
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is chromatographed on a column of silica gel, which
  9. washis eluted with methanol

Sources & evidence

ORD record
ord-e8803e72b6124f009271794781785578
Source dataset
uspto-grants-1979_03
Patent number
US04143048

Reaction notes

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