1,2-Dimethoxyethane → N-(1,1-Dimethylethyl)-4-[5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzenesulfonamide

HRID 446157Notes

Reaction equation

HRID 446157 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([F:25])[CH:18]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].S([CH2:36][N+:37]#[C-:38])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].COCCOC>CO>[C:1]([NH:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([F:25])[CH:18]=3)=[CH:38][N:37]=[CH:36]2)=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 11132250N-tert-Butyl-4-((3-fluoro-4-methoxybenzylidene)amino)benzenesulfonamide

Product 1

HCID 11784436N-(1,1-Dimethylethyl)-4-[5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzenesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-tert-butyl-4-[(3-fluoro-4-methoxybenzylidene)amino]benzenesulfonamide (41.5 g, 114 mmol, obtained in example 2), tosylmethylisocyanide (33.22 g, 171 mmol), K2CO3 (31.1 g, 228 mmol), DME (340 mL) and MeOH (778 mL) is heated at reflux for 3 h. The solvent is removed and the residue is taken up in a CHCl3/H2O mixture and the layers are separated. The aqueous phase is extracted with CHCl3 and the combined organic extracts are dried over MgSO4 and concentrated. A crude product is obtained, which is washed with Et2O several times to give 41.40 g of a creamy solid that is directly used in the next reaction (yield: 90%).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 h
  3. customThe solvent is removed
  4. customthe layers are separated
  5. extractionThe aqueous phase is extracted with CHCl3
  6. dry with materialthe combined organic extracts are dried over MgSO4
  7. concentrationconcentrated
  8. customA crude product is obtained
  9. washwhich is washed with Et2O several times

Sources & evidence

ORD record
ord-c567a15dfeef4be1b26c2c5d4ade956e
Source dataset
uspto-grants-2013_07
Patent number
US08476456B2

Reaction notes

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