Carbon Disulfide → HCID 12694981, compound

HRID 67967Notes

Reaction equation

HRID 67967 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[CH2:5][CH2:4][C@H:3]1[NH2:13].[C:14](=S)=[S:15]>C(O)C>[Br:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4][C@H:3]3[NH:13][C:14](=[S:15])[NH:1][C@@H:2]32)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 12694952Trans-1,2-diamino-7-bromo-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 12694981HCID 12694981, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trans-1,2-diamino-7-bromo-1,2,3,4-tetrahydronaphthalene (6.75 g, 28.0 m mol) was dissolved in ethanol (70 ml) and carbon disulfide (1.9 ml, 31.7 m mol) was added to the solution. After stirring at room temperature for 20 minutes, they were heated under reflux for 5.5 hours. The reaction mixture was cooled in an ice bath and crystals precipitated were collected by filtration, whereby trans-8-bromo-3a,4,5,9b-tetrahydronaphth[1,2-d]imidazoline-2-thione (5.57 g) was obtained in 70% yield. The crystals were recrystallized from methanol-acetonitrile to give pale-yellow crystals melting at 259.5°-260.5° C. (decomposition). The product gave the following data on spectroscopy and elemental analysis.

Workup

  1. temperaturethey were heated
  2. temperatureunder reflux for 5.5 hours
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. customcrystals precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f0c86e4bd77944dfb5b53e3dff19e272
Source dataset
uspto-grants-1982_08
Patent number
US04347369

Reaction notes

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