Water → 2-Methyl-4-(4-methylbenzene-1-sulfonyl)morpholine

HRID 2243239Notes

Reaction equation

HRID 2243239 reaction equation
[OH-].[Na+].O[CH:4]([CH3:30])[CH2:5][N:6]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:7][CH2:8][O:9]S(C1C=CC(C)=CC=1)(=O)=O.O>CO.C(Cl)Cl>[CH3:30][CH:4]1[O:9][CH2:8][CH2:7][N:6]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:5]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 72315987HCID 72315987, compound

Product 1

HCID 211064122-Methyl-4-(4-methylbenzene-1-sulfonyl)morpholine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium hydroxide (0.91 g, 0.02 mol) suspended in methanol (15 ml) was added to a stirred solution of Toluene-4-sulfonic acid 2-[(2-hydroxy-propyl)-(toluene-4-sulfonyl)-amino]-ethyl ester (9.69 g, 0.02 mol) in DCM (15 ml). After 1 h, water (50 ml) was added to the solution. The organic layer was collected, dried over sodium sulphate and evaporated in vaccuo to yield a green oily residue. This was purified by chromatographic separation (20% Ethyl acetate:petrol) to yield the title compound as a white solid. (1.70 g, 6.66 mmol, 33%).

Workup

  1. customThe organic layer was collected
  2. dry with materialdried over sodium sulphate
  3. customevaporated in vaccuo
  4. customto yield a green oily residue
  5. customThis was purified by chromatographic separation (20% Ethyl acetate:petrol)

Sources & evidence

ORD record
ord-c42c5e19c1634096a1667bd0f853452c
Source dataset
uspto-grants-2010_03
Patent number
US07674823B2

Reaction notes

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