Disodium → 6-(tert-Butyl-dimethylsilyloxy)-2-(3,5-dichlorophenyl)-dihydro-pyrazolo[1,2-alpha][1,2,4]triazole-1,3-dione

HRID 1838460Notes

Reaction equation

HRID 1838460 reaction equation
[Na][Na].[Cl:3][C:4]1[CH:5]=[C:6]([N:11]2[C:15](=[O:16])[NH:14][NH:13][C:12]2=[O:17])[CH:7]=[C:8]([Cl:10])[CH:9]=1.Br[CH2:19][CH:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:21]Br>CN(C=O)C>[Si:24]([O:23][CH:20]1[CH2:21][N:13]2[C:12](=[O:17])[N:11]([C:6]3[CH:5]=[C:4]([Cl:3])[CH:9]=[C:8]([Cl:10])[CH:7]=3)[C:15](=[O:16])[N:14]2[CH2:19]1)([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 141233DisodiumHCID 9996829Silane, [2-bromo-1-(bromomethyl)ethoxy](1,1-dimethylethyl)dimethyl-HCID 187550094-(3,5-Dichlorophenyl)-1,2,4-triazolidine-3,5-dione

Product 1

HCID 121120076-(tert-Butyl-dimethylsilyloxy)-2-(3,5-dichlorophenyl)-dihydro-pyrazolo[1,2-alpha][1,2,4]triazole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the disodium salt of 4-(3,5-dichlorophenyl)-[1,2,4]triazolidine-3,5-dione (7.65 g, 26.4 mmol) (Preparation 4) and 1,3-dibromo-2-(tert-butyldimethylsilyloxy)propane [11.7 g, 35.2 mmol; prepared according to Axenrod, et al. J. Org. Chem., Vol. 60 (1995), at pp. 1959-64] in DMF (160 ml) was heated under reflux for 2 h 45 min. The solvent was then removed under vacuum, and the resulting solid was chromatographed over silica gel (CH2Cl2) to yield the above compound as a white solid (2 g, mp=129° C.). 1H NMR (CDCl3): 7.51 (2H, m), 7.35 (1H, m), 4.52 (1H, br s), 3.95 (2H, d, J=11.6 Hz), 3.49 (2H, dd, J1=11.6 Hz, J2 =2 Hz), 0.81 (9H, s), 0.09 (6H, s).

Workup

  1. customprepared
  2. temperatureunder reflux for 2 h 45 min
  3. customThe solvent was then removed under vacuum
  4. customthe resulting solid was chromatographed over silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-d619892a0ef2433a9822ea2bb0a63207
Source dataset
uspto-grants-2004_01
Patent number
US06673825B2

Reaction notes

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