2-Isocyanatoethyl propionate → HCID 13053835, compound

HRID 1702870Notes

Reaction equation

HRID 1702870 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[S:7][C:6]=2[CH:11]=1.[C:12]([O:16][CH2:17][CH2:18][N:19]=[C:20]=[O:21])(=[O:15])[CH2:13][CH3:14]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C(C(C)=O)C>[C:12]([O:16][CH2:17][CH2:18][NH:19][C:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[S:7][C:6]=2[CH:11]=1)=[O:21])(=[O:15])[CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 1343472-Isocyanatoethyl propionateHCID 1390671,3-Benzoxathiol-2-one, 5-hydroxy-

Product 1

HCID 13053835HCID 13053835, compound

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-hydroxy-1,3-benzoxathiol-2-one (16.8 grams) was mixed with 2-(isocyanato)ethyl propionate (15.0 grams) and 10 drops of dibutyltin dilaurate in 200 milliliters of methyl ethyl ketone. The resulting solution was heated at reflux temperature for four hours and fifteen minutes, after which the solvent was removed by evaporation in vacuo, leaving a brown, viscous oil which crystallized upon standing at room temperature for 10 to 15 hours. The crude product was twice recrystallized from toluene. The purified compound, 5-[2-(propionyloxy)ethylcarbamoyloxy]-1,3-benzoxathiol-2-one, was a white, fibrous crystalline substance with a melting point of 78°-79° C. Elemental analysis calculated for C13H13NO6S (percent): carbon--50.15; hydrogen--4.21; nitrogen--4.50. Found: carbon--50.4; hydrogen--4.27; nitrogen--4.45.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux temperature for four hours
  3. customfifteen minutes, after which the solvent was removed by evaporation in vacuo
  4. customleaving a brown, viscous oil which
  5. customcrystallized
  6. customThe crude product was twice recrystallized from toluene

Sources & evidence

ORD record
ord-4d087224fe8f46fd89ab2ff34a13d087
Source dataset
uspto-grants-1982_09
Patent number
US04349685

Reaction notes

Loading…