Triethylamine → Methanesulfonic acid 5-nitro-pyridin-2-ylmethyl ester

HRID 43150Notes

Reaction equation

HRID 43150 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19]O)=[N:17][CH:18]=1)([O-:12])=[O:11].C(N(CC)CC)C>C(Cl)Cl>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][O:5][S:2]([CH3:1])(=[O:4])=[O:3])=[N:17][CH:18]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 20583228(5-Nitropyridin-2-yl)methanol

Product 1

HCID 86641144Methanesulfonic acid 5-nitro-pyridin-2-ylmethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Methanesulfonic anhydride (1.79 g, 10.3 mmol, 1.1 equiv) was added portionwise to a cold (5° C.) mixture of (5-nitro-pyridin-2-yl)-methanol (Step 112.4) (1.44 g, 9.4 mmol) and triethylamine (1.57 mL, 11.3 mmol, 1.2 equiv) in DCM (20 mL), under an argon atmosphere. The reaction mixture was allowed to stir for 0.5 h at 5° C., quenched with H2O and extracted with DCM. The organic phase was washed with H2O, dried (Na2SO4), filtered and concentrated to provide 2.16 g of the title compound as a brown solid: ESI-MS: 231.1 [M−H]−; tR=2.85 min (System 1).

Workup

  1. customquenched with H2O
  2. extractionextracted with DCM
  3. washThe organic phase was washed with H2O
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a0539809da9a4c12b09466ef0ec3c822
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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