Water → 4'-(4-Chloro-5-formyl-2-phenylimidazol-1-ylmethyl)biphenyl-2-sulfonic acid dimethylaminomethylenamide

HRID 1019246Notes

Reaction equation

HRID 1019246 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:6]=1[CH:7]=[O:8].[CH3:15][N:16]([CH:18]=[N:19][S:20]([C:23]1[C:24]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35]Br)=[CH:31][CH:30]=2)=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21])[CH3:17].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:17][N:16]([CH:18]=[N:19][S:20]([C:23]1[C:24]([C:29]2[CH:30]=[CH:31][C:32]([CH2:35][N:5]3[C:6]([CH:7]=[O:8])=[C:2]([Cl:1])[N:3]=[C:4]3[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:33][CH:34]=2)=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 541617064'-Bromomethylbiphenyl-2-sulfonic acid dimethylaminomethylenamideHCID 178520008HCID 178520008, compound

Product 1

HCID 867577064'-(4-Chloro-5-formyl-2-phenylimidazol-1-ylmethyl)biphenyl-2-sulfonic acid dimethylaminomethylenamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 g of 4-chloro-5-formyl-2-phenylimidazole (Chem. Pharm. Bull. 1976, 24(5), 960), 3.8 g of 4′-bromomethylbiphenyl-2-sulfonic acid dimethylaminomethylenamide (J. Med. Chem. 1995, 38, 2357) and 2.8 g of K2CO3 were stirred at RT for 30 h in 50 ml of DMF. The reaction mixture was poured onto 500 ml of water and extracted 2 times using 250 ml of EA each time. The organic phase was then washed with 100 ml of water and dried over MgSO4, and the solvent was removed in vacuo. Chromatography on silica gel using MTB yielded 1.9 g of a white, crystalline powder, mp 193° C.

Workup

  1. extractionextracted 2 times
  2. washThe organic phase was then washed with 100 ml of water
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customChromatography on silica gel using MTB yielded 1.9 g of a white, crystalline powder, mp 193° C.

Sources & evidence

ORD record
ord-d1e9163aae7a4bea856f3572f93277bf
Source dataset
uspto-grants-2002_11
Patent number
US06486189B2

Reaction notes

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