Hydrochloric Acid → N-(5-amino-2-methylpyridin-3-yl)methanesulfonamide

HRID 1812429Notes

Reaction equation

HRID 1812429 reaction equation
C1(C(=[N:14][C:15]2[CH:16]=[C:17]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([CH3:21])=[N:19][CH:20]=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C1COCC1>[NH2:14][C:15]1[CH:16]=[C:17]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([CH3:21])=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86647089N-(5-(Diphenylmethyleneamino)-2-methylpyridin-3-YL)methanesulfonamide

Product 1

HCID 66600561N-(5-amino-2-methylpyridin-3-yl)methanesulfonamideYield 29.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-(diphenylmethyleneamino)-2-methylpyridin-3-yl)methanesulfonamide (0.430 g, 1.177 mmol) in THF (10 mL) was added hydrochloric acid (JT Baker) (1.765 mL, 1.765 mmol) (1N). The reaction was stirred at rt in closed system for 20 min. The reaction mixture was partitioned between EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (40 g, 5% to 10% MeOH in DCM) to afford the desired product as a brown solid (70.0 mg). MS (ESI pos. ion) m/z: 202.1. 1H NMR (300 MHz, CDCl3) δ ppm 2.42 (s, 3H) 3.03 (s, 3H) 3.70 (br. s., 2H) 6.15 (br. s., 1H) 7.20 (d, J=2.34 Hz, 1H) 7.87 (d, J=2.34 Hz, 1H).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and sat. NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layer were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (40 g, 5% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-577857ad1d994e4d9d6e8caa731e71bf
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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