Hydrochloric Acid → 1028-11-1

HRID 1661510Notes

Reaction equation

HRID 1661510 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9].C(N(CC)CC)C.C[O-].[Na+].Cl>C1COCC1.ClCCl>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([S:17]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)(=[O:19])=[O:18])=[CH:15][CH:16]=1)([O-:10])=[O:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 104392-AminopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 6117091028-11-1Yield 47.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-aminopyridine 9 (2.00 g, 21.3 mmol) in THF (45 mL) were successively added dichloromethane (88 mL), 4-nitrobenzenesulfonyl chloride (9.89 g, 44.6 mmol), and triethylamine (6.51 mL, 46.75 mmol). The solution was heated to reflux for 2 h and the resultant light yellow solid was collected by filtration. This material was suspended in 200 mL of methanol and a large excess (>10 eq) of sodium methoxide was added. The mixture was stirred at r.t. for 6 h, treated with HCl 1N (2 mL) and concentrated in vacuo at 80° C. to 50 mL volume. This solution was transferred into an Erlenmeyer flask and further neutralized with 1N HCl. A precipitate was formed which was collected by filtration, washed with water and dried, to afford the title compound 10 (2.8 g, 47% yield). 1H NMR (DMSO-d6) δ (ppm): 8.32 (d, J=6.8 Hz, 2H), 8.07 (d, J=7.0 Hz, 2H), 7.92 (bs, 1H), 7.80 (bs, 1H), 7.26 (bs, 1H), 6.85 (bs, 1H). LRMS (ESI): (calc) 279.03 (found) 280.0 (MH+).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 2 h
  3. filtrationthe resultant light yellow solid was collected by filtration
  4. concentrationconcentrated in vacuo at 80° C. to 50 mL volume
  5. customA precipitate was formed which
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-5072d107788248c09107bb2701f4c7bf
Source dataset
uspto-grants-2011_10
Patent number
US08030344B2

Reaction notes

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