HCID 178470431, compound → HCID 178470430, compound

HRID 1954762Notes

Reaction equation

HRID 1954762 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:9]=[N:10][NH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])=[C:4]([N+:20]([O-])=O)[CH:3]=1>C(O)C.C(Cl)(Cl)Cl.O=[Pt]=O>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:9]=[N:10][NH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])=[C:4]([NH2:20])[CH:3]=1

Participants

5

Reactant 1

HCID 178470431HCID 178470431, compound

Product 1

HCID 178470430HCID 178470430, compoundYield 108.4%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×HCID 6212ChloroformSolvent

Procedure

A suspension of PtO2 (541.6 mg) in ethanol (50 mL) was shaken under hydrogen (40 psi) in a PARR™ hydrogenator for 19 hours. A solution of ethyl 4-(4-chloro-2-nitrobenzoyl)-1H-1,2,3-triazole-5-carboxylate (1.014 g, 3.124 mmol) in chloroform (10 mL)/ethanol (200 mL) was then added to the reaction mixture and shaking on the PARR™ hydrogenator at 51 psi was continued. After 3 hours the reaction mixture was filtered through a pad of CELITE™, washing with ethanol. The filtrate was concentrated under vacuum (0.3 torr) to afford 0.998 g (108%) of crude title compound as a bright yellow foam.

Workup

  1. stirringshaking on the PARR™ hydrogenator at 51 psi
  2. filtrationAfter 3 hours the reaction mixture was filtered through a pad of CELITE™
  3. washwashing with ethanol
  4. concentrationThe filtrate was concentrated under vacuum (0.3 torr)

Sources & evidence

ORD record
ord-4070a17cacde497b8a91b7e47b4e0d47
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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