o-Toluenesulfonyl Isocyanate → Succinic anhydride

HRID 344634Notes

Reaction equation

HRID 344634 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 8028TetrahydrofuranSolvent

Procedure

16.1 g of polypropylene glycol (M=480), 65.7 g of anhydrous tetrahydrofuran and 0.22 g of toluenesulfonyl isocyanate were stirred for 15 minutes in a three-necked flask with a capacity of 250 ml. 13 g of tolylene-2,4-diisocyanate and 0.17 g of dibutyltin dilaurate were then added and the mixture was heated under reflux for two hours. 6.9 g of the addition product formed from 1 mol of succinic anhydride and 1 mol of diethanolamine were then added and refluxing was continued for a further two hours. The solution was then diluted with 42.2 g of tetrahydrofuran and 1.95 g of polyoxypropylenediamine (M=420) in 42.2 g of tetrahydrofuran were added dropwise.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for two hours

Sources & evidence

ORD record
ord-8316ee8fd5524f158a48a69ea30674ab
Source dataset
uspto-grants-1991_10
Patent number
US05053317

Reaction notes

Loading…