Water → trans-3a,4,5,9b-Tetrahydronaphth[1,2-d]imidazoline-2-thione

HRID 67965Notes

Reaction equation

HRID 67965 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C@H:3]1[NH2:12].O.[C:14](=S)=[S:15]>C(O)C>[NH:1]1[C@@H:2]2[C:11]3[C:6]([CH2:5][CH2:4][C@H:3]2[NH:12][C:14]1=[S:15])=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 3

HCID 962WaterHCID 6348Carbon DisulfideHCID 12694946Trans-1,2-diamino-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 12694975trans-3a,4,5,9b-Tetrahydronaphth[1,2-d]imidazoline-2-thioneYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trans-1,2-diamino-1,2,3,4-tetrahydronaphthalene (461 mg, 2.84 m mol) was dissolved in ethanol (8 ml), water (4 ml) was added to the solution, then carbon disulfide (190 μl, 3.17 m mol) was added thereto under stirring at room temperature. The mixture was heated under reflux for 4 hours and cooled in an ice-water bath. The crystals precipitating out were separated by filtration, washed with ether and dried in vacuum to give trans-3a,4,5,9b-tetrahydronaphth[1,2-d]imidazoline-2-thione (350 mg, 1.71 m mol) in 60% yield. The data spectroscopy and elemental analysis were as follows:

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled in an ice-water bath
  4. customThe crystals precipitating out
  5. customwere separated by filtration
  6. washwashed with ether
  7. customdried in vacuum

Sources & evidence

ORD record
ord-cf447936f9cf46a789663253ae495e00
Source dataset
uspto-grants-1982_08
Patent number
US04347369

Reaction notes

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