Chlorosulfonyl isocyanate → 2-(1,2,3-Thiadiazol-4-yl)phenyl isocyanatosulfonate

HRID 1632441Notes

Reaction equation

HRID 1632441 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[S:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:10]=[N:9]1>C1(C)C=CC=CC=1>[N:5]([S:2]([O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]1[N:10]=[N:9][S:8][CH:12]=1)(=[O:4])=[O:3])=[C:6]=[O:7]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 27674472-(1,2,3-Thiadiazol-4-yl)phenol

Product 1

HCID 203987932-(1,2,3-Thiadiazol-4-yl)phenyl isocyanatosulfonateYield 88.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

By the procedure of Example 1, 7.9 g of chlorosulfonyl isocyanate was reacted with 10 g of 2-(1,2,3-thiadiazol-4-yl)phenol [prepared by the procedure of U.S. Pat. No. 3,940,407] in 125 ml of dry toluene. The reaction mixture was stirred at 25° C. for 1 hour, then heated at 100° to 110° C. for 1 hour. The resulting solution was cooled to 25° C., filtered, and the filtrate was concentrated in vacuo to yield 14 g of the title compound as a crude oil. The IR showed an isocyanate absorption at 2220 cm-1.

Workup

  1. customprepared by the procedure of U.S
  2. temperatureheated at 100° to 110° C. for 1 hour
  3. temperatureThe resulting solution was cooled to 25° C.
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-37c53eb1db0441adbeadea676237c8ec
Source dataset
uspto-grants-1984_10
Patent number
US04475944

Reaction notes

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