Sodium Chloride → 4-Bromo-3-(methanesulfonylamino)-benzoic acid methyl ester

HRID 746767

Reaction equation

HRID 746767 reaction equation
[O-:1][S:2]([O-:5])(=O)=O.[Na+].[Na+].[CH3:8][O:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[C:13]([NH2:18])[CH:12]=1.[CH3:20]CN(CC)CC.[Na+].[Cl-]>ClCCl>[CH3:8][O:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[C:13]([NH:18][S:2]([CH3:20])(=[O:5])=[O:1])[CH:12]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 24436Sodium SulfateHCID 3928639Methyl 3-amino-4-bromobenzoate

Product 1

HCID 692544444-Bromo-3-(methanesulfonylamino)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add Na2SO4 (0.12 mmol) to a suspension of 4-Bromo-3-amino-benzoic acid methyl ester (0.1 mmol) and Et3N (0.1 mmol) in dichloromethane at 0° C. Stir 4 h at RT. Add a saturated solution of NaCl (15 mL), and extract with dichloromethane (2×50 mL). Dry over NaSO4, filter and evaporate to dryness. Purify the residue utilizing flash chromatography (Silica gel-hexane/EtOAc) to provide the title compound.

Workup

  1. extractionextract with dichloromethane (2×50 mL)
  2. dry with materialDry over NaSO4
  3. filtrationfilter
  4. customevaporate to dryness
  5. customPurify the residue utilizing flash chromatography (Silica gel-hexane/EtOAc)

Sources & evidence

ORD record
ord-b097c323dd0c44d9ba4d4ac2d7d18996
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Linked notes

Loading…