(2-Bromophenyl)methanesulfonyl chloride → 1-(2-Bromophenyl)-N-methylmethanesulfonamide

HRID 1523755Notes

Reaction equation

HRID 1523755 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9](Cl)(=[O:11])=[O:10].[CH3:13][NH2:14].O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9]([NH:14][CH3:13])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 2761452(2-Bromophenyl)methanesulfonyl chlorideHCID 13000549Methanamine--water (1/1)

Product 1

HCID 143717641-(2-Bromophenyl)-N-methylmethanesulfonamideYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-bromophenyl)methanesulfonyl chloride (2 g, 7 mmol) in THF (15 mL) was added CH3NH2/H2O (25%, 2 g, 20 mmol) at 0° Celsius. The resulting mixture was warmed up to rt, stirred for 16 hours, concentrated to dryness and purified by HPLC to give the title compound (0.8 g, 41%). MS (ESI): mass calcd. for C8H8BrO2S, 262.96; m/z found, 264.0 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 7.65-7.54 (m, 2H), 7.35 (m, 1H), 7.22 (dd, J=7.6, 1.7, 1H), 4.53 (s, 2H), 4.10 (s, 1H), 2.72 (s, 3H).

Workup

  1. concentrationconcentrated to dryness
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-ff14a1eeadf94120ae13cec3acfc4f50
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…