4-Methoxybenzenesulfonyl chloride → HCID 705729, compound

HRID 343973Notes

Reaction equation

HRID 343973 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 1N 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 1N hydrochloric acid solution, water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-427304d855e74ba4ac140dee6240b040
Source dataset
uspto-grants-1999_01
Patent number
US05863949

Reaction notes

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