Toluene → Methyl acetate hexane

HRID 653551Notes

Reaction equation

HRID 653551 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1S(N)(=O)=O)([O-])=[O:2].NCP(=O)(OC(C)C)[O:17][CH:18](C)C.[C:26]1([CH3:32])C=CC=CC=1>>[C:26]([O:17][CH3:18])(=[O:2])[CH3:32].[CH3:8][CH2:9][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 3

HCID 1140TolueneHCID 1385102-NitrobenzenesulfonamideHCID 13740526Dipropan-2-yl (aminomethyl)phosphonate

Product 1

HCID 23449302Methyl acetate hexane

Procedure

10 g (0.58 mole) of 2-nitrophenylsulfonamide are suspended in 20 ml of toluene and heated to reflux temperature. 17.0 g (0.087 mole) of diisopropyl aminomethylphosphonate are added dropwise to the hot solution. The reaction mixture is then boiled under reflux for 10 hours, cooled and evaporated. Chromatographing the residue over silica gel with a 4:1 methyl acetate/hexane mixture gives 1.6 g of 2-(di-i-propoxyphosphonylmethylamino)-phenylsulfonamide in the form of a yellow oil.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature
  3. temperatureunder reflux for 10 hours
  4. temperaturecooled
  5. customevaporated

Sources & evidence

ORD record
ord-f0454959cd19471f87064f43432f0e9c
Source dataset
uspto-grants-1987_06
Patent number
US04677217

Reaction notes

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