HCID 59715988, compound → 2-(4-bromo-N-methylsulfonylanilino)acetic acid

HRID 2223784Notes

Reaction equation

HRID 2223784 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:13][C:14]([OH:16])=[O:15])[S:9]([CH3:12])(=[O:10])=[O:11])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 59715988HCID 59715988, compound2×

Product 1

HCID 8754662-(4-bromo-N-methylsulfonylanilino)acetic acidYield 95.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of tert-butyl [(4-bromophenyl)(methylsulfonyl) amino]acetate (intermediate 2, 1.00 g, 2.74 mmol) and silica gel (13.7 g) in toluene (88 mL) was heated at reflux for 4 h. The reaction was cooled to room temperature and filtered, the filter cake was washed with methanol/dichloromethane (20/80; 2×100 mL). Evaporation of the combined organic filtrates gave the title compound as a white solid (0.81 g, 95%). LC/MS: 2.81 min; z/e 325 and 327, calcd (M+18) 325 and 327. 1H NMR (400 MHz: MeOD): 7.45 (2H), 7.35 (2H), 4.45 (2H), 3.05 (3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. filtrationfiltered
  4. washthe filter cake was washed with methanol/dichloromethane (20/80; 2×100 mL)
  5. customEvaporation of the combined organic filtrates

Sources & evidence

ORD record
ord-81698daa2b3743ec95d4d609c1ae2943
Source dataset
uspto-grants-2008_05
Patent number
US07375248B2

Reaction notes

Loading…