4-Methoxybenzenesulfonyl chloride → HCID 17866403, compound

HRID 583296Notes

Reaction equation

HRID 583296 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>O1CCOCC1.O.C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH:1][C:2]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])(=[O:29])=[O:28])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 753164-Methylanthranilic acid

Product 1

HCID 17866403HCID 17866403, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a room temperature solution of 2-amino-4-methyl benzoic acid (1.93 g, 12.8 mmol) in 20 ml of dioxane:H2O (1:1) containing triethylamine (2.68 ml, 19.2 mmol), was added 4-methoxybenzenesulfonyl chloride (2.91 g, 14.1 mmol). The mixture was stired at rt for 18 hr. The resulting mixture was diluted with methylene chloride, washed with 1N HCl, H2O, brine, dried and concentrated. The crude liquid was triturated with 16 ml of EtOAc: hexane (1:3) to afford 2.358 g of the desired product as a white solid (57%). Electrospray Mass Spec 322 (M+H).

Workup

  1. washwashed with 1N HCl, H2O, brine
  2. customdried
  3. concentrationconcentrated
  4. customThe crude liquid was triturated with 16 ml of EtOAc: hexane (1:3)

Sources & evidence

ORD record
ord-2c0cb3826230448a87f787344b42c244
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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