Benzoic acid, 3-(chlorosulfonyl)- → 3-{[[(3-Bromophenyl)methyl](methyl)amino]sulfonyl}benzoic acid

HRID 564567

Reaction equation

HRID 564567 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.Cl[S:12]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([OH:20])=[O:19])(=[O:14])=[O:13]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH3:10])[S:12]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([OH:20])=[O:19])(=[O:14])=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 457588Benzenemethanamine, 3-bromo-N-methyl-

Product 1

HCID 578132513-{[[(3-Bromophenyl)methyl](methyl)amino]sulfonyl}benzoic acidYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Bromophenyl)-N-methylmethanamine (0.100 g, 0.5 mmol) in DCM (5 mL) was added TEA (0.139 mL, 1.000 mmol) and 3-(chlorosulfonyl)benzoic acid (0.110 g, 0.500 mmol). The resulting mixture was stirred at room temperature for 0.5 h. The reaction was quenched with HCl (1 N), concentrated and redissolved in EtOAc (10 mL) which was washed with H2O (2×3 mL), brine (3 mL), then dried with Na2SO4. It was then filtered and concentrated to afford the title compound (0.1505 g, 78%). LC-MS m/z 384 (M+H)+.

Workup

  1. customThe reaction was quenched with HCl (1 N)
  2. concentrationconcentrated
  3. dissolutionredissolved in EtOAc (10 mL) which
  4. washwas washed with H2O (2×3 mL), brine (3 mL)
  5. dry with materialdried with Na2SO4
  6. filtrationIt was then filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-caa4573a80e24f40a34fe6341b29b0f6
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

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