Hydrazine hydrate (1:1) → 5-chloro-2-(3-glycylaminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone hydrate

HRID 1391285Notes

Reaction equation

HRID 1391285 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[C:20]([CH3:21])=[N:19][N:18]=[C:17]2[CH2:22][NH:23][C:24](=[O:37])[CH2:25][N:26]2C(=O)C3=CC=CC=C3C2=O)=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].O.NN>C(O)C>[OH2:8].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[C:20]([CH3:21])=[N:19][N:18]=[C:17]2[CH2:22][NH:23][C:24](=[O:37])[CH2:25][NH2:26])=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 155678715-chloro-2-[3-(2-phthalimidoacetamidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-benzophenone

Product 1

HCID 213257385-chloro-2-(3-glycylaminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone hydrateYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-chloro-2-[3-(2-phthalimidoacetamidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-benzophenone (2.3 g) in ethanol (20 ml), hydrazine hydrate (0.92 g) is added, and the resultant mixture is refluxed for 1 hour. The precipitated phthalylhydrazide is filtered off, and the filtrate is evaporated under reduced pressure. The residue is dissolved in methylene chloride, washed with saturated aqueous sodium bicarbonate and water in order, dried over sodium sulfate, and evaporated under reduced pressure. The residue is chromatographed on a column of silica gel, and the product obtained from the eluate by evaporation is recrystallized from ethyl acetate to give 5-chloro-2-(3-glycylaminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone hydrate as crystals melting at 110° to 113° C. The yield is 94%.

Workup

  1. filtrationThe precipitated phthalylhydrazide is filtered off
  2. customthe filtrate is evaporated under reduced pressure
  3. dissolutionThe residue is dissolved in methylene chloride
  4. washwashed with saturated aqueous sodium bicarbonate and water in order
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue is chromatographed on a column of silica gel
  8. customthe product obtained from the
  9. customeluate by evaporation
  10. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0b6fd17b75ca42c3a0d3c1a6902971c3
Source dataset
uspto-grants-1979_02
Patent number
US04141901

Reaction notes

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