4-(Chlorosulfonyl)benzoic acid → 4-{[(2,4-Dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}benzoic acid

HRID 401830

Reaktionsgleichung

Reaktionsgleichung von HRID 401830
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[CH2:5][NH:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].Cl[S:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=1)(=[O:31])=[O:30]>C1COCC1>[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[CH2:5][N:6]([C:7]1[S:8][CH:9]=[CH:10][N:11]=1)[S:29]([C:32]1[CH:33]=[CH:34][C:35]([C:36]([OH:38])=[O:37])=[CH:39][CH:40]=1)(=[O:31])=[O:30]

Komponenten

5

Edukt 3

HCID 823854-(Chlorosulfonyl)benzoic acidHCID 2733832Lithium HexamethyldisilazideHCID 49931979N-(2,4-dimethoxybenzyl)thiazol-2-amine

Produkt 1

HCID 577319334-{[(2,4-Dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}benzoic acidAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

N-(2,4-dimethoxybenzyl)-1,3-thiazol-2-amine (3.83 g, 0.0153 mol; Icagen) was dissolved in THF (70 mL, 0.8 mol) and cooled in an ice bath. 1.0 M of Lithium hexamethyldisilazide in THF (33 mL) was added dropwise to the reaction. After 30 minutes, a solution of 4-(chlorosulfonyl)benzoic acid (3.07 g, 0.0139 mol) in THF (30 mL, 0.4 mol) was added dropwise to the reaction. The reaction was stirred overnight then quenched with 0.5 N HCl and diluted with ethyl acetate. The phases were separated and the organic phase was washed with 2× with 0.5N HCl. The organic phase was dried over magnesium sulfate, treated with activated carbon and filtered through Celite. The filtrate was evaporated to a residue and triturated with ethyl acetate. The solid was collected by filtration. Vacuum drying afforded the product as a tan solid (2.55 g, 40%).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customthen quenched with 0.5 N HCl
  3. additiondiluted with ethyl acetate
  4. customThe phases were separated
  5. washthe organic phase was washed with 2× with 0.5N HCl
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. additiontreated with activated carbon
  8. filtrationfiltered through Celite
  9. customThe filtrate was evaporated to a residue
  10. customtriturated with ethyl acetate
  11. filtrationThe solid was collected by filtration
  12. customVacuum drying

Quellen und Nachweise

ORD-Eintrag
ord-4774b3533e2744c88a0cce3dec151b25
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741934B2

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