Chlorosulfonyl isocyanate → HCID 13647651, compound

HRID 1906564Notes

Reaction equation

HRID 1906564 reaction equation
[C:1]1([C:6]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[NH:10][C:9]2=[O:18])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[Cl:19][S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21]>C(#N)C>[Cl:19][S:20]([NH:23][C:24]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:8]([C:6](=[O:7])[C:1]2[S:5][CH:4]=[CH:3][CH:2]=2)[C:9]1=[O:18])=[O:25])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 13565658HCID 13565658, compound

Product 1

HCID 13647651HCID 13647651, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred slurry of 1.5 g. (5.4 mmole) of 3-(2-thenoyl)-5-chloro-2-oxindole in 15 ml. of dry acetonitrile was added 0.52 ml. (5.9 mmole) of chlorosulfonyl isocyanate, and the reaction mixture was stirred at room temperature for 2 hours. A small sample was removed, filtered and evaporated in vacuo to give a small sample of N-chlorosulfonyl-3-(2- thenoyl)-5-chloro-2-oxindole-1-carboxamide, mp 166°-169° C. To the remainder of the reaction mixture, 30 ml. of water was added slowly with stirring and stirring was continued for 1 hour. The reaction mixture was then poured into 50 ml. of 1N hydrochloric acid containing ice chips, and the resulting mixture was stirred for 20 minutes. The yellow solid was recovered by filtration, washed with water and diisopropyl ether and recrystallized from glacial acetic acid to give 200 mg. of a first crop of the title compound, mp 213°-215° C. The mother liquors from which the first crop had been recovered deposited a further yellow solid. The latter solid was recovered by filtration to give 470 mg. of a second crop of the title compound. The second crop was recrystallized from glacial acetic acid and combined with the first crop and recrystallized from glacial acetic acid. This gave 280 mg. of the title compound, mp 232°-234° C.

Workup

  1. customA small sample was removed
  2. filtrationfiltered
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-92f6d6ab8e8f4e12a7080420282b746f
Source dataset
uspto-grants-1987_03
Patent number
US04652658

Reaction notes

Loading…