2-Thiazolidinone,4-thioxo- → HCID 178508330, compound

HRID 436858Notes

Reaction equation

HRID 436858 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[S:7])[CH2:4][S:3]1.[NH:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=N)[NH:10]1>CO>[NH:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[C:4]2[S:3][C:2](=[O:1])[NH:6][C:5]2=[S:7])[NH:10]1

Participants

4

Reactant 2

HCID 15395952-Thiazolidinone,4-thioxo-HCID 178508669HCID 178508669, compound

Product 1

HCID 178508330HCID 178508330, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 49.7 parts of 2-oxo-4-thioxothiazolidine in 990 parts of methanol there was added at 40° C. and under an atmosphere of nitrogen 54.3 parts of powdered 1,3-diiminoisoindoline. Initially, a thick slurry resulted. The reaction mixture was stirred at room temperature for two hours during which time the mixture gradually thinned. The mixture was then heated at reflux for approximately two hours and after cooling to 25° C., was filtered. The collected solid was washed with fresh methanol and dried in vacuo at 50° C. to obtain 1-imino-3-(2-oxo-4-thioxo-5-thiazolidinylidene)isoindoline as an orange powder melting at 267°-8° C. (dec.).

Workup

  1. customInitially, a thick slurry resulted
  2. temperatureThe mixture was then heated
  3. temperatureat reflux for approximately two hours
  4. temperatureafter cooling to 25° C.
  5. filtrationwas filtered
  6. washThe collected solid was washed with fresh methanol
  7. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-22216317c05d493e81fdc0e0761e14fe
Source dataset
uspto-grants-1977_06
Patent number
US04028372

Reaction notes

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