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

HRID 2308973Notes

Reaction equation

HRID 2308973 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 (0.196 mol) of 1,2-diamino-2-methylpropane in 300 ml of chloroform and 80 ml pyridine at 0° C. was added 10 g (0.057 mol) of benzenesulfonyl chloride 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-a14a12c255124b849e5fdbfdf6095138
Source dataset
uspto-grants-1987_09
Patent number
US04692446

Reaction notes

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