(1,2-Dibromoethyl)benzene → HCID 20395139, compound

HRID 261141Notes

Reaction equation

HRID 261141 reaction equation
[Na][Na].[C:3]([C:5]([SH:10])=[C:6]([C:8]#[N:9])[SH:7])#[N:4].Br[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13]Br>>[C:8]([C:6]1[S:7][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[S:10][C:5]=1[C:3]#[N:4])#[N:9]

Participants

4

Reactant 3

HCID 7145(1,2-Dibromoethyl)benzeneHCID 141233DisodiumHCID 410077HCID 410077, compound

Product 1

HCID 20395139HCID 20395139, compound

Conditions

Temperature
40 °C

Procedure

To a stirred suspension of 18.6 g of the disodium salt of 1,2-dicyano-1,2-dimercaptoethylene under nitrogen is added 26.4 g of 1,2-dibromo-1-phenylethane. After stirring at 40° C. for one-half hour, the mixture is heated under reflux for 1.5 hours, cooled, filtered, and the solvent removed under reduced pressure. The residue is crystallized by filtration with carbon tetrachloride to give the product, 2,3-dicyano-5,6-dihydro-5-phenyl-p-dithiin, as golden brown crystals, melting point 121.5° C. to 124° C. A purified sample had melting point 125° C. to 126.5° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue is crystallized by filtration with carbon tetrachloride

Sources & evidence

ORD record
ord-ece68ca7359148e084677d8aec88ebce
Source dataset
uspto-grants-1979_08
Patent number
US04164404

Reaction notes

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