Sulfuryl chloride → N,N'-Bis(2,4,4-trimethylpentan-2-yl)sulfuric diamide

HRID 1381276Notes

Reaction equation

HRID 1381276 reaction equation
[C:1]([NH2:9])([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].[S:10](Cl)(Cl)(=[O:12])=[O:11]>CCCCCC>[C:1]([NH:9][S:10]([NH:9][C:1]([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2])(=[O:12])=[O:11])([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 61017tert-Octylamine

Product 1

HCID 221350N,N'-Bis(2,4,4-trimethylpentan-2-yl)sulfuric diamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

The starting N,N'di-t-octylsulfamide is prepared from commercially available t-octylamine and sulfuryl chloride using either the method of Stowell (J. C. Stowell, J. Org. Chem. 32, p.2360, 1967) or of Timberlake (J. W. Timberlake, J. Alender, A. W. Garner, M. L. Hodges, C. Ozmeral and S. Syilagyi, J. Org. Chem. 46, p.2082-2089, 1981). The reaction is preferably run in hexane and the product isolated as a hexane solution. The hexane solution of the sulfamide can be concentrated prior to oxidizing the sulfamide or it can be concentrated during the oxidation.

Workup

  1. concentrationThe hexane solution of the sulfamide can be concentrated
  2. concentrationcan be concentrated during the oxidation

Sources & evidence

ORD record
ord-1a76bb9e647d487e8de2fa91cc3e56c9
Source dataset
uspto-grants-1986_04
Patent number
US04585857

Reaction notes

Loading…