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

HRID 2291899Notes

Reaction equation

HRID 2291899 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 mol) 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 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 was recrystalized 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. customwas recrystalized from toluene

Sources & evidence

ORD record
ord-dc46f45a31724e7abf93ac210be00658
Source dataset
uspto-grants-1989_01
Patent number
US04798892

Reaction notes

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