Chlorosulfonyl isocyanate → 2-(1,2-Oxazol-3-yl)phenyl sulfurisocyanatidate

HRID 1632438Notes

Reaction equation

HRID 1632438 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])=[N:2]1.Cl[S:14]([N:17]=[C:18]=[O:19])(=[O:16])=[O:15]>C1(C)C=CC=CC=1>[N:17]([S:14]([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:3]1[CH:4]=[CH:5][O:1][N:2]=1)(=[O:16])=[O:15])=[C:18]=[O:19]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 1357631582-ISOXAZOL-3-YL-PHENOL

Product 1

HCID 134243222-(1,2-Oxazol-3-yl)phenyl sulfurisocyanatidateYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution containing 30 g of 2-(isoxazol-3-yl)phenol [prepared by the procedure of R. Beugelmans and C. Morin, J. Org. Chem., 42, 1356 (1977)] in 200 ml of dry toluene was added slowly 26.3 g of chlorosulfonyl isocyanate while maintaining the temperature at 20° to 30° C. with external cooling. The resulting suspension containing a while solid was stirred at 25° C. for 1 hour, then heated at 100° to 110° C. for 1 hour. The resulting slightly cloudy solution was cooled to 25° C., filtered, and the filtrate was concentrated in vacuo to yield 45 g of the title compound as a crude oil. The IR spectrum showed an isocyanate absorption at 2220 cm-1.

Workup

  1. customprepared by the procedure of R
  2. temperaturewhile maintaining the temperature at 20° to 30° C. with external cooling
  3. additionThe resulting suspension containing a while solid
  4. temperatureheated at 100° to 110° C. for 1 hour
  5. temperatureThe resulting slightly cloudy solution was cooled to 25° C.
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8cfe785bbcaa4c599680530511e66de7
Source dataset
uspto-grants-1984_10
Patent number
US04475944

Reaction notes

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