Ethanol → HCID 22758658, compound

HRID 1704721Notes

Reaction equation

HRID 1704721 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:11])=[C:5]2[C:9](=O)[CH:8]=[CH:7][C:6]=12.[K].[C:13](=[O:16])([O-])[O-].[NH4+:17].[NH4+:18].[CH2:19]([OH:21])C>O>[Cl:1][C:2]1[S:3][C:4]([Cl:11])=[C:5]2[C:9]3([C:19](=[O:21])[NH:18][C:13](=[O:16])[NH:17]3)[CH:8]=[CH:7][C:6]=12

Participants

6

Reactant 4

HCID 702EthanolHCID 395859HCID 395859, compoundHCID 517111Ammonium CarbonateHCID 5462222Potassium

Product 1

HCID 22758658HCID 22758658, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.900 g (4.30 mmol) of 1,3-dichloro-cyclopenta(c) thiophene-4-one (MacDowall et. al., J. Org. Chem., 32, 1226 (1967) 0.488 g (7.50 mmol) of potassium cycnide and 3.30 g (34 mmol) of powdered ammonium carbonate were heated with 25 ml of 50% aqueous ethanol at 110°-120° C. in a steel bomb for 16 hours. The reaction mixture was cooled, diluted with 200 ml of water, boiled for 10 to 15 minutes, then cooled and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo to a tan solid (0.980 g) which was crystallized from ethyl acetate to give 0.600 g (50%) of 1,3-dichloro-spiro[cyclopenta(c)thiophene-4,4'-imidazolidine]-2',5'-dione, mp 239°-241° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a tan solid (0.980 g) which
  8. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-fb3122dcd6fe4c31b425569690a3d010
Source dataset
uspto-grants-1978_11
Patent number
US04127665

Reaction notes

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