3,4-Dimethoxybenzenesulfonyl chloride → HCID 24994808, compound

HRID 1258622Notes

Reaction equation

HRID 1258622 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[C:10]([NH2:13])[N:9]=2)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24](Cl)(=[O:26])=[O:25])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>N1C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24]([NH:13][C:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[S:12][N:11]=2)(=[O:25])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 27947575-(4-chlorophenyl)-1,2,4-thiadiazol-3-amine

Product 1

HCID 24994808HCID 24994808, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-(4-chlorophenyl)-1,2,4-thiadiazol-3-amine (423 mg, 2.0 mmol) in 10 mL of dry pyridine was added 529 mg (2.23 mmol) of 3,4-dimethoxybenzenesulfonyl chloride. The solution was stirred at room temperature under Argon. After 21 h, the pyridine was removed in vacuo and flashed off with toluene. The residue was partitioned between EtOAc and 1M NaOH. The organic phase was washed with 1M NaOH until no turbidity was observed on rectification of a small sample. The alkaline phase was made acidic (˜pH 3) with 1M HCl and extracted with EtOAc. EtOH was used in the second extraction to assist solubilizing the sulfonamide. After drying over Na2SO4, solvent was removed in vacuo. The crude crystalline product weighed 0.45 g. The crude product was taken up in 13 mL of hot HOAc, diluted with 7 mL of H2O and seeded to give white needles (384 mg) after collection by filtration, washing with H2O, and drying in vacuo. The product had mp 220-221° C.

Workup

  1. customthe pyridine was removed in vacuo
  2. customThe residue was partitioned between EtOAc and 1M NaOH
  3. washThe organic phase was washed with 1M NaOH until no turbidity
  4. extractionextracted with EtOAc
  5. extractionEtOH was used in the second extraction
  6. dry with materialAfter drying over Na2SO4, solvent
  7. customwas removed in vacuo
  8. additiondiluted with 7 mL of H2O

Sources & evidence

ORD record
ord-ae5eb72ab29043e99eaf62c31d0a8d33
Source dataset
uspto-grants-2013_06
Patent number
US08466182B2

Reaction notes

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