Diethyl Ether → N'-(2-Amino-2-methylpropyl)-N,N-dimethylsulfuric diamide

HRID 2308979Notes

Reaction equation

HRID 2308979 reaction equation
[NH2:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4].CCOCC.[CH3:12][N:13]([CH3:18])[S:14](Cl)(=[O:16])=[O:15]>C(N(CC)CC)C>[CH3:4][C:3]([NH2:6])([CH3:5])[CH2:2][NH:1][S:14]([N:13]([CH3:18])[CH3:12])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 131282-MethylpropylenediamineHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 13603865N'-(2-Amino-2-methylpropyl)-N,N-dimethylsulfuric diamideYield 60.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 30.7 g (0.35 mole) of 1,2-diamino-2-methylpropane, 150 ml of ether and 50 ml of triethylamine was cooled to 0° C. and 20 g (0.14 mole) of dimethylsulfamoylchloride was added slowly. The mixture was stirred for 30 min. and then concentrated under reduced pressure. The residue was mised with water, basified with potassium carbonate and concentrated to dryness. Acetone was added and insoluble material was removed by filtration. Concentration of the filtrate gave a solid, which crystallized from toluene to give 16.5 g (60%) of product, m.p. 77°-78° C. The IR and MNR spectra were consistent with the assigned structure.

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationconcentrated to dryness
  3. additionAcetone was added
  4. custominsoluble material was removed by filtration
  5. customConcentration of the filtrate gave a solid, which
  6. customcrystallized from toluene

Sources & evidence

ORD record
ord-75f41e40db9e40d3bb629e4428ebf97b
Source dataset
uspto-grants-1987_09
Patent number
US04692446

Reaction notes

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