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Pyruvic Acid → 2',5-dichloro-3-(3-pyruvamidomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone

HRID 25946
Notes
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Reaction equation

HRID 25946 reaction equation
[C:1]([OH:6])(=O)[C:2]([CH3:4])=[O:3].S(Cl)(Cl)=O.Br.Br.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:36])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([N:28]2[C:32]([CH3:33])=[N:31][N:30]=[C:29]2[CH2:34][NH2:35])[CH:22]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.CN(C)C=O.C1C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:36])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([N:28]2[C:32]([CH3:33])=[N:31][N:30]=[C:29]2[CH2:34][NH:35][C:1](=[O:6])[C:2]([CH3:4])=[O:3])[CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 1060Pyruvic AcidHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 213256842',5-dichloro-3-(3-aminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone dihydrobromide

Product 1

HCID 213257442',5-dichloro-3-(3-pyruvamidomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenoneYield 64.8%

Reagents, catalysts & solvents

4
HCID 241BenzeneSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of pyruvic acid (0.33 g) and thionyl chloride (0.27 g) in chloroform (2 ml) is refluxed for 1 hour. After cooling, the solution is mixed with 2',5-dichloro-3-(3-aminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone dihydrobromide (1.31 g), benzene (6 ml) and dimethylformamide (11 ml) at 0° C. The resultant mixture is stirred at room temperature for 3 hours and allowed to stand overnight. The reaction mixture is neutralized with aqueous sodium bicarbonate and shaken with ethyl acetate. The organic layer is washed with water, dried and evaporated to remove the solvent. The residue is recrystallized from ethyl acetate to give 2',5-dichloro-3-(3-pyruvamidomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone (0.7 g) as crystals melting at 178° to 180° C.

Workup

  1. temperatureAfter cooling
  2. washThe organic layer is washed with water
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9ffa1233d3a54301a7b399e8045faf43
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04147700

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes