Hydrochloric Acid → 3-cyano-N-(1,2,4-thiadiazol-5-yl)-4-[2-iodo-4-(trifluoromethoxy)phenoxy]benzenesulfonamide

HRID 46370Notes

Reaction equation

HRID 46370 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].[C:20]([C:22]1[CH:23]=[C:24]([S:29]([NH:32][C:33]2[S:37][N:36]=[CH:35][N:34]=2)(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1F)#[N:21].Cl>CS(C)=O.C(OCC)(=O)C>[C:20]([C:22]1[CH:23]=[C:24]([S:29]([NH:32][C:33]2[S:37][N:36]=[CH:35][N:34]=2)(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1[O:13][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:7][C:2]=1[I:1])#[N:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27694112-Iodo-4-(trifluoromethoxy)phenolHCID 580423023-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

Product 1

HCID 594365983-cyano-N-(1,2,4-thiadiazol-5-yl)-4-[2-iodo-4-(trifluoromethoxy)phenoxy]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-iodo-4-(trifluoromethoxy)phenol (Preparation 226, 600 mg, 1.97 mmol) and potassium carbonate (1125 mg, 8.14 mmol) in Dimethylsulfoxide (10 mL) was added 3-cyano-4-fluoro-N-[1,2,4]thiadiazol-5-yl-benzenesulfonamide (Preparation 65). The reaction was heated to 80° C. under N2 for 7 hours before the addition of ethyl acetate (20 mL) and 3M aqueous HCl solution (30 mL). The organic layer was collected, washed with brine (20 mL), dried over sodium sulphate and concentrated in vacuo. The residue was triturated in dichloromethane and filtered to afford 965 mg of the title compound.

Workup

  1. customThe organic layer was collected
  2. washwashed with brine (20 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in dichloromethane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-fe75e3f41a77445d8b90cb62f7c10b93
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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