HCID 12112004, compound → HCID 10298927, compound

HRID 1838462Notes

Reaction equation

HRID 1838462 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:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][O:26][CH:27]([CH2:30]Cl)[CH2:28]Br)=[CH:21][CH:20]=1>CN(C=O)C>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][O:26][CH:27]2[CH2:30][N:13]3[C:12](=[O:17])[N:11]([C:6]4[CH:5]=[C:4]([Cl:3])[CH:9]=[C:8]([Cl:10])[CH:7]=4)[C:15](=[O:16])[N:14]3[CH2:28]2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 12112004HCID 12112004, compoundHCID 69902224HCID 69902224, compound

Product 1

HCID 10298927HCID 10298927, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3,5-dichlorophenyl)-[1,2,4]triazolidine-3,5-dione disodium salt (1.5 g, 5.17 mmol) (Preparation 4) and 1-Bromo-4-(2-bromo-1-chloromethyl-ethoxymethyl)-benzene (1.95 g, 5.69 mmol) (Preparation 1) in DMF (25 ml) was heated under reflux for 2 h 30 min. The solvent was removed under vacuum, and water was added to the resulting material. The precipitate was washed with diethyl ether and chromatographed over silica gel (CH2Cl2) to yield the above compound as a white solid (366 mg, mp=142° C.). 1H NMR (CDCl3):7.44 (2H, d, J=8.3 Hz), 7.3-7.4 (3H, m), 7.09 (2H, d, J=8.3 Hz), 4.43 (2H, s), 4.15-4.35 (3H, m), 3.49 (2H, dd, J1=12.2 Hz, J2=2.2 Hz).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h 30 min
  3. customThe solvent was removed under vacuum, and water
  4. additionwas added to the resulting material
  5. washThe precipitate was washed with diethyl ether
  6. customchromatographed over silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-5ab58a65b35e4ac1b6c0ede01569b78f
Source dataset
uspto-grants-2004_01
Patent number
US06673825B2

Reaction notes

Loading…