4-Methoxybenzenesulfonyl chloride → HCID 705729, compound

HRID 1857364Notes

Reaction equation

HRID 1857364 reaction equation
O.[Na+].[Na+].[NH:4]=[CH:5][C:6]([O-:8])=[O:7].N=[CH:10][C:11]([O-:13])=[O:12].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>O1CCOCC1.O.C(Cl)Cl>[C:6]([CH2:5][N:4]([CH2:10][C:11]([OH:13])=[O:12])[S:29]([C:26]1[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=1)(=[O:31])=[O:30])([OH:8])=[O:7]

Participants

7

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 131721096HCID 131721096, compound

Product 1

HCID 705729HCID 705729, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of iminoacetic acid disodium salt monohydrate (5.0 grams, 25.6 mmol) in dioxane (50 ml) and water (50 ml) was added triethylamine (5.3 ml, 38 mmol) followed by 4-methoxybenzenesulfonyl chloride (5.8 grams, 28.0 mmol). The mixture was stirred overnight at room temperature and diluted with methylene chloride. The solution was washed with 1 N hydrochloric acid solution, water and brine, dried over magnesium sulfate and concentrated under vacuum leaving [carboxymethyl(4-methoxybenzenesulfonyl)amino]acetic acid as a white solid, 3.83 grams (49%).

Workup

  1. washThe solution was washed with 1 N hydrochloric acid solution, water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-88c5e7eb005e498d95c6defefdab910b
Source dataset
uspto-grants-2000_11
Patent number
US06147074

Reaction notes

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