Pyridine → Methyl 4-methoxy-3-(morpholinosulfonyl)benzoate

HRID 1801579Notes

Reaction equation

HRID 1801579 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:8]([O:10][CH3:11])=[O:9])(=[O:4])=[O:3].N1C=CC=CC=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C(Cl)Cl.CCOC(C)=O>[CH3:16][O:15][C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[S:2]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 8083MorpholineHCID 2794613Methyl 3-(chlorosulfonyl)-4-methoxybenzoate

Product 1

HCID 711627Methyl 4-methoxy-3-(morpholinosulfonyl)benzoateYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-(chlorosulfonyl)-4-methoxybenzoate 40 (1.002 g, 3.8 mmol) in CH2Cl2 (20 mL) at 0° C. was added pyridine (0.46 mL, 6 mmol) and morpholine (0.395 mL, 5 mmol). The reaction mixture was warmed to room temperature, stirred for 30 min, and diluted with EtOAc. The organic phase was washed with NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 0% to 20% EtOAc in CH2Cl2) gave methyl 4-methoxy-3-(morpholinosulfonyl)benzoate 41 (0.970 g, 81% yield) as a white solid. Mass spectrum: calculated for C13H17NO6S 315.1. found 316.1 (M++1).

Workup

  1. washThe organic phase was washed with NaHCO3 (1×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography on silica gel (eluted with 0% to 20% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-369d462af51d4b8f9adbe145cdcbb0d6
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

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