3,4-Dimethoxybenzenesulfonyl chloride → HCID 178492882, compound

HRID 1258613Notes

Reaction equation

HRID 1258613 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([NH2:12])=[N:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23](Cl)(=[O:25])=[O:24])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>N1C=CC=CC=1.CC(O)=O.O>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23]([NH:12][C:9]2[NH:10][N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)(=[O:24])=[O:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

6

Reactant 2

HCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 178509136HCID 178509136, compound

Product 1

HCID 178492882HCID 178492882, compoundYield 50.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 5-phenyl-4H-1,2,4-triazol-3-amine (354 mg, 2 mmol) in dry pyridine (10 mL) was added 3,4-dimethoxybenzenesulfonyl chloride (529 mg, 2.23 mmol). The solution was stirred at room temperature under Argon. After 48 h, the pyridine was removed in vacuo and flashed off with toluene. The residue was partitioned between CH2Cl2 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 CH2Cl2. After drying over Na2SO4, the solvent was removed in vacuo to give 0.47 g crude product. The crude product was dissolved in hot HOAc (22 mL), diluted with water (9 mL) and seeded. The product was collected by filtration, washed with water, then EtOH and dried in vacuo to give 361 mg of a granular white solid, mp 245-246° C.

Workup

  1. customthe pyridine was removed in vacuo
  2. customThe residue was partitioned between CH2Cl2 and 1M NaOH
  3. washThe organic phase was washed with 1M NaOH until no turbidity
  4. extractionextracted with CH2Cl2
  5. dry with materialAfter drying over Na2SO4
  6. customthe solvent was removed in vacuo
  7. customto give 0.47 g crude product
  8. filtrationThe product was collected by filtration
  9. washwashed with water
  10. dry with materialEtOH and dried in vacuo

Sources & evidence

ORD record
ord-841623df56814f5586c02752be8f17f3
Source dataset
uspto-grants-2013_06
Patent number
US08466182B2

Reaction notes

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