Hydrochloric Acid → HCID 13910345, compound

HRID 542591Notes

Reaction equation

HRID 542591 reaction equation
[C:1]1([C:6]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:17])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:25]([N:33]=[C:34]=[O:35])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>CS(C)=O.O>[C:25]([NH:33][C:34]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[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:17])=[O:35])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 78210Benzoyl isocyanateHCID 13565654HCID 13565654, compound

Product 1

HCID 13910345HCID 13910345, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 486 mg (2.0 mmole) of 3-(2-thenoyl)-2-oxindole and 445 mg (4.4 mmole) of triethylamine in 5 ml of dimethyl sulfoxide was added 324 mg (2.2 mmole) of benzoyl isocyanate. Stirring was continued for 1 hour, and then the mixture was poured into a mixture of 50 ml of water and 1.7 ml of 3N hydrochloric acid. The resulting mixture was cooled in an ice-bath and the solid was removed by filtration. The solid was recrystallized from ca. 30 ml of 2:1 ethanol:water to give 190 mg of the title compound as fluffy, yellow crystals, mp 165°-166° C. (dec).

Workup

  1. temperatureThe resulting mixture was cooled in an ice-bath
  2. customthe solid was removed by filtration
  3. customThe solid was recrystallized from ca. 30 ml of 2:1 ethanol

Sources & evidence

ORD record
ord-4c0c133d67504b6fab08b78621971f0e
Source dataset
uspto-grants-1987_04
Patent number
US04658037

Reaction notes

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