Cornforth reagent → HCID 19825135, compound

HRID 727825Notes

Reaction equation

HRID 727825 reaction equation
[C:1]([C:3]1[N:4]([S:19](=[O:24])(=[O:23])[N:20]([CH3:22])[CH3:21])[CH:5]=[C:6]([CH:8]([OH:18])[C:9]2[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=2[Cl:17])[N:7]=1)#[N:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[C:1]([C:3]1[N:4]([S:19](=[O:24])(=[O:23])[N:20]([CH3:22])[CH3:21])[CH:5]=[C:6]([C:8](=[O:18])[C:9]2[C:10]([Cl:17])=[CH:11][C:12]([Cl:16])=[CH:13][C:14]=2[Cl:15])[N:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 19825140HCID 19825140, compound

Product 1

HCID 19825135HCID 19825135, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Cyano-1-(dimethylsulphamoyl)-4-(2,4,6-trichloro-α-hydroxybenzyl)imidazole (15.7 g) was dissolved in dichloromethane and pyridinium dichromate (28.9 g) and silica gel (230-400 mesh; 58 9) added and the mixture stirred for 11 hours. The mixture was filtered and the precipitate washed with dichloromethane. The filtrate and washings were evaporated under reduced pressure and the residue washed with diisopropyl ether and dried under reduced pressure to give 2-cyano-1-(dimethylsulphamoyl)4-(2,4,6-trichlorobenzoyl)imidazole, m.p. 142°-151°. (Compound 5).

Workup

  1. filtrationThe mixture was filtered
  2. washthe precipitate washed with dichloromethane
  3. customThe filtrate and washings were evaporated under reduced pressure
  4. washthe residue washed with diisopropyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-52a7911477234c7f8078eeebbf41578c
Source dataset
uspto-grants-1991_09
Patent number
US05045557

Reaction notes

Loading…