Potassium Carbonate → HCID 86682480, compound

HRID 509105Notes

Reaction equation

HRID 509105 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].C(=O)([O-])[O-].[K+].[K+].[C:16]([C:18]1[CH:19]=[C:20]([S:25]([N:28]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=2[O:43][CH3:44])[C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1F)#[N:17]>CN(C)C(=O)C>[C:16]([C:18]1[CH:19]=[C:20]([S:25]([N:28]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=2[O:43][CH3:44])[C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1[S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])#[N:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23642ThioguaiacolHCID 580422543-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

Product 1

HCID 86682480HCID 86682480, compoundYield 231.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-Methoxythiophenol (0.0322 g, 0.230 mmol) and potassium carbonate (0.158 g, 1.14 mmol) were stirred in N,N-dimethylacetamide. 3-Cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 1, 0.248 g, 0.571 mmol) was added to the reaction mixture portion-wise and the mixture stirred under a nitrogen atmosphere at ambient temperature for 2 hours. The reaction was quenched with a 1M aqueous solution of sodium hydroxide (100 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was separated and washed with water (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The oil was purified by silica gel column chromatography (ethyl acetate elution) to afford the title compound (0.295 g, 93%) and this was used without further purification.

Workup

  1. customThe reaction was quenched with a 1M aqueous solution of sodium hydroxide (100 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. customThe organic layer was separated
  4. washwashed with water (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil
  9. customThe oil was purified by silica gel column chromatography (ethyl acetate elution)

Sources & evidence

ORD record
ord-b3931c06229d4667b1fd3bc445642fcc
Source dataset
uspto-grants-2015_08
Patent number
US09096558B2

Reaction notes

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