2-Nitrobenzenesulfonyl chloride → HCID 69119040, compound

HRID 1814811Notes

Reaction equation

HRID 1814811 reaction equation
C(=O)([O-])O.[Na+].[CH3:6][C@H:7]1[CH2:12][NH:11][CH2:10][CH2:9][NH:8]1.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23])([O-:15])=[O:14]>O.CC(C)=O>[CH3:6][C@H:7]1[CH2:12][N:11]([S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N+:13]([O-:15])=[O:14])(=[O:23])=[O:24])[CH2:10][CH2:9][NH:8]1

Participants

6

Reactant 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 27342192-Methylpiperazine, (S)-

Product 1

HCID 69119040HCID 69119040, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Sodium hydrogen carbonate (21.7 g) and acetone (50 ml) was added to a solution of (S)-(+)-2-methylpiperazine (6.0 g) in water (75 ml). The resulting suspension was cooled (0-5° C.) and a solution of 2-nitrobenzenesulphonyl chloride (15.9 g) in acetone (25 ml) was added, the reaction mixture was allowed to stir at ambient temperature overnight. Water (60 ml) was added and volatile material was removed by evaporation. The residue was acidified to pH 2 by the addition of HCl (2 M, 75 ml) and the mixture was extracted into DCM (2×100 ml). The aqueous phase was adjusted to pH 10-11 by the addition of NaOH (2 M, 50 ml) and extracted into EtOAc (2×150 ml). The organic washings were combined, dried and concentrated to leave the title compound (14.1 g) as a yellow oil. NMR: 1.06 (d, 3H), 2.35-2.43 (m,1H), 2.73-3.06 (m, 4H), 3.65-3.71 (m, 2H), 7.59-7.62 (m, 1H), 7.68-7.72 (m, 2H), 7.95-7.98 (m, 1H); m/z (+ve ESP): 286 (M+H)+.

Workup

  1. customvolatile material was removed by evaporation
  2. additionThe residue was acidified to pH 2 by the addition of HCl (2 M, 75 ml)
  3. extractionthe mixture was extracted into DCM (2×100 ml)
  4. additionThe aqueous phase was adjusted to pH 10-11 by the addition of NaOH (2 M, 50 ml)
  5. extractionextracted into EtOAc (2×150 ml)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7d9a5508af044a2db807f47473542a56
Source dataset
uspto-grants-2005_04
Patent number
US06878712B1

Reaction notes

Loading…