Potassium Carbonate → 3-Cyano-4-[2-iodo-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 46338Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]1[CH:10]=[C:11]([S:16]([NH:19][C:20]2[S:24][N:23]=[CH:22][N:21]=2)(=[O:18])=[O:17])[CH:12]=[CH:13][C:14]=1F)#[N:8].[I:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1[OH:36]>CS(C)=O.C(OCC)(=O)C>[C:7]([C:9]1[CH:10]=[C:11]([S:16]([NH:19][C:20]2[S:24][N:23]=[CH:22][N:21]=2)(=[O:18])=[O:17])[CH:12]=[CH:13][C:14]=1[O:36][C:27]1[CH:28]=[CH:29][C:30]([C:32]([F:33])([F:34])[F:35])=[CH:31][C:26]=1[I:25])#[N:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of potassium carbonate (0.850 g, 0.006150 mol) and 3-cyano-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 65, 0.500 g, 0.001759 mol) in dimethyl sulfoxide (5.0 mL) was added 2-iodo-4-(trifluoromethyl)phenol (Preparation 224, 0.595 g, 0.002066 mol) and stirred at 80° C. under nitrogen for 16 hours. The reaction mixture was diluted with ethyl acetate (10.0 mL) and the organic phase was washed with saturated aqueous sodium chloride solution (2×10.0 mL), dried over sodium sulphate, filtered and concentrated in vacuo. The residue was triturated in ethyl acetate (5.0 mL) to yield title compound as a white solid, 560 mg, 58% yield.

Workup

washthe organic phase was washed with saturated aqueous sodium chloride solution (2×10.0 mL)
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was triturated in ethyl acetate (5.0 mL)

Sources & evidence

ORD record: ord-b2df462de7aa44e4b77efbd319b3e644
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541588B2

Reaction notes

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