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

HRID 252207

Reaction equation

HRID 252207 reaction equation
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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-98e7c2aab3264f9c8d39a0a5a61ac333
Source dataset
uspto-grants-2011_01
Patent number
US07868026B2

Linked notes

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