Benzenesulfonyl chloride → N-(2-Amino-2-methylpropyl)benzenesulfonamide

HRID 1380591Notes

Reaction equation

HRID 1380591 reaction equation
[NH2:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4].[C:7]1([S:13](Cl)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:4][C:3]([NH2:6])([CH3:5])[CH2:2][NH:1][S:13]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 131282-Methylpropylenediamine

Product 1

HCID 23046101N-(2-Amino-2-methylpropyl)benzenesulfonamideYield 79.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 14.97 g (0.169 mol) of 1,2-diamino-2-methylpropane in 300 ml of chloroform and 80 ml pyridine was added 10 g (0.057 mol) of benzenesulfonyl cloride at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes and allowed to reach room temperature. The mixture was evaporated to dryness in vacuo and the residue was partitioned between water and chloroform. Evaporation of the chloroform gave 10.3 g (79%) of semisolid. The product was identified by NMR and IR spectroscopy and elemental analysis.

Workup

  1. customto reach room temperature
  2. customThe mixture was evaporated to dryness in vacuo
  3. customthe residue was partitioned between water and chloroform
  4. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-3582140b21024839b67edee648677a1f
Source dataset
uspto-grants-1986_04
Patent number
US04582855

Reaction notes

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