3-Aminopyridine → Methyl 2-[(pyridin-3-ylamino)sulfonyl]benzoate

HRID 252207

Reaktionsgleichung

Reaktionsgleichung von HRID 252207
Cl[S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1>CC#N.CCOC(C)=O.CCOCC>[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][S:2]([C:5]2[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3])[CH:16]=1

Komponenten

6

Edukt 2

HCID 100093-AminopyridineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl ester

Produkt 1

HCID 4354882Methyl 2-[(pyridin-3-ylamino)sulfonyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 2-(chlorosulfonyl)benzoate (14.1 g, 60.0 mmol) was added to a stirred solution of 3-pyridinamine (15.0 g, 159.4 mmol) in CH3CN (0.4 M). The temperature rose to 25° C. and a small amount of reddish oil separated out. CHCl3 (2.0 M, protected with amylenes) was added to return all materials to solution. After 1 h, the solvents were evaporated and the residual oil was partitioned between EtOAc and water. The organic layer was washed with water and was evaporated to give the crude product. The crude product was dissolved in the minimum amount of hot EtOAc and was diluted with ether. The product rapidly crystallized out and after 1 hour filtered off and washed with ether to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 8.38 (d, 1H) 8.31 (d, 2H) 7.93 (d, 2H) 7.80 (d, 2H) 7.76 (t, 1H) 7.64 (t, 1H) 7.53 (t, 1H) 7.25 (m, 1H) 4.12 (s, 3H).

Aufarbeitung

  1. customrose to 25° C.
  2. customa small amount of reddish oil separated out
  3. additionCHCl3 (2.0 M, protected with amylenes) was added
  4. customthe solvents were evaporated
  5. customthe residual oil was partitioned between EtOAc and water
  6. washThe organic layer was washed with water
  7. customwas evaporated
  8. customto give the crude product
  9. customThe product rapidly crystallized out and after 1 hour
  10. filtrationfiltered off
  11. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-98e7c2aab3264f9c8d39a0a5a61ac333
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868026B2

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