Potassium Carbonate → HCID 86682481, compound

HRID 509106Notes

Reaction equation

HRID 509106 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([N:13]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[C:14]2[S:18][N:17]=[CH:16][N:15]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH3:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([SH:44])=[CH:40][CH:39]=1>CN(C)C(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([S:10]([N:13]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[C:14]2[S:18][N:17]=[CH:16][N:15]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[S:44][C:41]1[CH:42]=[CH:43][C:38]([O:37][CH3:36])=[CH:39][CH:40]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 580422543-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

Product 1

HCID 86682481HCID 86682481, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-Cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 1, 0.100 g, 0.230 mmol) and potassium carbonate (0.0668 g, 0.483 mmol) were stirred in N,N-dimethylacetamide (3 mL). 4-Methoxythiophenol (0.0322 g, 0.230 mmol) was added to the reaction mixture and stirred under a nitrogen atmosphere at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with a 1M aqueous solution of sodium hydroxide, then brine (×3). The organic layer was dried, filtered and concentrated in vacuo to afford the title compound as a solid (0.13 g, 100%), which was used without purification.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with a 1M aqueous solution of sodium hydroxide
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee56fd366bca413e9d41d748660b29fa
Source dataset
uspto-grants-2015_08
Patent number
US09096558B2

Reaction notes

Loading…