Isopropylamine → N,N'-diisopropylsulfamide

HRID 2413118Notes

Reaction equation

HRID 2413118 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C([N:7]([CH2:10][CH3:11])CC)C.[CH3:12][Si](C)(C)Cl.[S:17](Cl)(Cl)(=[O:19])=[O:18]>C1COCC1>[CH:1]([NH:4][S:17]([NH:7][CH:10]([CH3:11])[CH3:12])(=[O:19])=[O:18])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 24648Sulfuryl chloride

Product 1

HCID 2818101N,N'-diisopropylsulfamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

29.5 parts of isopropylamine and 55.6 parts of triethylamine were introduced into 320 parts of THF. 60 parts of trimethylchlorosilane were added a little at a time at from 0° to -5° C. under nitrogen and the mixture was stirred at room temperature for 30 minutes and at 60° C. for 1 hour and then cooled to -10° C. 33.8 parts of sulfuryl chloride were added a little at a time and the mixture was allowed to warm to room temperature and was then stirred for 2 hours. The trimethylchlorosilane and the solvent were distilled off and the residue was washed with ice-water. 30.5 parts of N,N'-diisopropylsulfamide of melting point 98°-101° C. (starting substance) were obtained.

Workup

  1. temperaturecooled to -10° C
  2. temperatureto warm to room temperature
  3. stirringwas then stirred for 2 hours
  4. distillationThe trimethylchlorosilane and the solvent were distilled off
  5. washthe residue was washed with ice-water

Sources & evidence

ORD record
ord-537efb687c614dd997e9a19df243bc62
Source dataset
uspto-grants-1985_01
Patent number
US04496563

Reaction notes

Loading…