Water → ethyl 3-[(methylsulfonyl)amino]benzoate

HRID 1991232Notes

Reaction equation

HRID 1991232 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(=O)([O-])O.[Na+].[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>O1CCOCC1>[CH3:18][S:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11400Ethyl 3-aminobenzoateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 670300ethyl 3-[(methylsulfonyl)amino]benzoateYield 81.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 3-aminobenzoate (2.0 g, 12.1 mmol) and sodium hydrogen carbonate (1.2 g, 14.5 mmol) in 1,4-dioxane (24 ml) was added methanesulphonyl chloride (2.3 ml, 30.3 mmol). The mixture was stirred at room temperature for 3 h, before addition of water (10 ml), and the reaction mixture was stirred for a further 5 days. The mixture was partitioned between ethyl acetate and hydrochloric acid (2M) and the organic phase was separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was passed through a plug of silica, eluting with ethyl acetate/cyclohexane [1:3] and the filtrate was concentrated in vacuo to give the title compound (2.4 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and hydrochloric acid (2M)
  2. customthe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. washeluting with ethyl acetate/cyclohexane [1:3]
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6cbff6797ada49b58238597696d4f6ab
Source dataset
uspto-grants-2010_01
Patent number
US07645786B2

Reaction notes

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