Potassium Carbonate → 4-(4-chloro-2-iodophenoxy)-N-(5-chloro-1,3-thiazol-2-yl)-3-cyanobenzenesulfonamide

HRID 1401969Notes

Reaction equation

HRID 1401969 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[S:21][C:20]([N:22](CC2C=CC(OC)=CC=2OC)[S:23]([C:26]2[CH:31]=[CH:30][C:29](F)=[C:28]([C:33]#[N:34])[CH:27]=2)(=[O:25])=[O:24])=[N:19][CH:18]=1.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:29]2[CH:30]=[CH:31][C:26]([S:23]([NH:22][C:20]3[S:21][C:17]([Cl:16])=[CH:18][N:19]=3)(=[O:24])=[O:25])=[CH:27][C:28]=2[C:33]#[N:34])=[C:4]([I:9])[CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 6202344-Chloro-2-iodophenolHCID 59436479N-(5-Chloro-1,3-thiazol-2-yl)-3-cyano-N-(2,4-dimethoxybenzyl)-4-fluorobenzenesulfonamide

Product 1

HCID 594364884-(4-chloro-2-iodophenoxy)-N-(5-chloro-1,3-thiazol-2-yl)-3-cyanobenzenesulfonamideYield 72%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 4-chloro-2-iodophenol (305 mg, 1.20 mmol) and potassium carbonate (207 mg, 1.5 mmol) in dimethyl sulphoxide (5.0 ml) was added N-(5-chloro-1,3-thiazol-2-yl)-3-cyano-N-(2,4-dimethoxybenzyl)-4-fluorobenzenesulfonamide (Preparation 207, 468 mg, 1.00 mmol). Suspension stirred at room temperature for 18 hours. The reaction mixture was poured into ethyl acetate (20 ml) and saturated aqueous ammonium chloride solution (20 ml) and the aqueous layer extracted with ethyl acetate (3×20 ml). Combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The crude residue was dissolved in dichloromethane (5 ml), trifluoroacetic acid (5 ml) was added and the reaction mixture was stirred at room temperature for 2 hours. The solvent was concentrated in vacuo and purified by ISCO™ preparative system eluting with dichloromethane:ethyl acetate (gradient 1:0 to 6:4, by volume) to afford the title compound as a solid, 396 mg, 72% yield.

Workup

  1. extractionthe aqueous layer extracted with ethyl acetate (3×20 ml)
  2. dry with materialCombined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude residue was dissolved in dichloromethane (5 ml)
  5. additiontrifluoroacetic acid (5 ml) was added
  6. stirringthe reaction mixture was stirred at room temperature for 2 hours
  7. concentrationThe solvent was concentrated in vacuo
  8. custompurified by ISCO™ preparative system
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-9ca04cffa7aa42f79a7ae8a0c4b8d6b9
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Reaction notes

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