o-Toluenesulfonyl Isocyanate → Succinic anhydride

HRID 344633Notes

Reaction equation

HRID 344633 reaction equation
C1(C)C(S([N:10]=C=O)(=O)=[O:8])=CC=CC=1.[C:14]([O-:27])(=[O:26])[CH2:15][CH2:16][CH2:17]CCCCCCCC.[C:28]([O-:41])(=O)[CH2:29]CCCCCCCCCC.C([Sn+2]CCCC)CCC>O1CCCC1>[C:14]1(=[O:27])[O:26][C:17](=[O:8])[CH2:16][CH2:15]1.[NH:10]([CH2:15][CH2:14][OH:27])[CH2:29][CH2:28][OH:41]

Participants

5

Reactant 2

HCID 2733313o-Toluenesulfonyl IsocyanateHCID 9809426Di-n-butyldilauryltin

Product 2

HCID 7922Succinic anhydrideHCID 8113Diethanolamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

17.8 g of polypropylene glycol (M=480), 0.24 g of toluenesulfonyl isocyanate and 150 g of anhydrous tetrahydrofuran were stirred for 15 minutes in a three-necked flask with a capacity of 250 ml. 13.0 g of tolylene 2,4-diisocyanate and 0.17 g of dibutyltin dilaurate were then added, the mixture was refluxed for one hour, and the solution obtained was added dropwise to a mixture of 7.6 g of the monoamide formed from 1 mol of succinic anhydride and 1 mol of diethanolamine in 184 g of tetrahydrofuran and heated for 22 hours under reflux until isocyanate was no longer present in the solution. A weight average of the molecular weight (Mw) of 8500 was determined with the aid of gel permeation chromatography (polystyrene standard).

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. customthe solution obtained
  3. additionwas added dropwise to a mixture of 7.6 g of the monoamide

Sources & evidence

ORD record
ord-5667f9862ce34edbb9735d7d70c8bc9a
Source dataset
uspto-grants-1991_10
Patent number
US05053317

Reaction notes

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