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

HRID 1380594Notes

Reaction equation

HRID 1380594 reaction equation
[NH2:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4].[CH3:7][N:8]([CH3:13])[S:9](Cl)(=[O:11])=[O:10]>CCOCC>[CH3:4][C:3]([NH2:6])([CH3:5])[CH2:2][NH:1][S:9]([N:8]([CH3:13])[CH3:7])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 131282-MethylpropylenediamineHCID 83372Dimethylsulphamoyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 30.7 g (0.35 mol) of 1,2-diamino-2-methylpropane, 150 ml of ether and 50 ml of trienthylamine was cooled to 0° C. and 20 g (0.14 mol) of dimethylsulfamoyl chloride was added slowly. The reaction mixture was stirred for 30 minutes and evaporated to dryness. The residue was mixed with water, basified with K2CO3 and evaporated to dryness. Acetone was added and the mixture was filtered. Evaporation of the filtrate gave a solid which recrystallized from toluene to give 16.5 g (60.3%) of product, mp 77°-78° C. The NMR and IR were consistent with the assigned structure.

Workup

  1. customevaporated to dryness
  2. additionThe residue was mixed with water
  3. customevaporated to dryness
  4. additionAcetone was added
  5. filtrationthe mixture was filtered
  6. customEvaporation of the filtrate
  7. customgave a solid which
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-8f22c815e62345a28b339e85ec1a608b
Source dataset
uspto-grants-1986_04
Patent number
US04582855

Reaction notes

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