Water → HCID 12694983, compound

HRID 67966Notes

Reaction equation

HRID 67966 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C@H:3]1[NH2:13].[C:14](=S)=[S:15].O>C(O)C>[F:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C@H:2]1[NH:1][C:14](=[S:15])[NH:13][C@@H:3]1[CH2:4][CH2:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 6348Carbon DisulfideHCID 12694972Trans-1,2-diamino-6-fluoro-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 12694983HCID 12694983, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trans-1,2-diamino-6-fluoro-1,2,3,4-tetrahydronaphthalene (3.84 g, 21.3 m mol) was dissolved in ethanol (40 ml) and carbon disulfide (1.4 ml, 23.4 m mol) was added to the solution. After the resulting white suspension was stirred for a while, water (20 ml) was added to the suspension and they were heated under reflux for 30 minutes. The reaction mixture was cooled with ice and the precipitate was filtered. The solid was washed in turn with water (three portions of 20 ml, totaling 60 ml), ethyl ether (20 ml) and n-hexane (50 ml) and dried under vacuum to give trans-7-fluoro-3a,4,5,9b-tetrahydronaphth[1,2-d]imidazoline-2-thione as a yellowish grey solid (3.88 g, 17.4 m mol) in 82% yield. The product was recrystallized from acetone-acetonitrile to give light-yellow needles melting at 256.5° to 257.5° C. (decomposition). The data on spectroscopy were as follows:

Workup

  1. additionwas added to the suspension and they
  2. temperaturewere heated
  3. temperatureunder reflux for 30 minutes
  4. temperatureThe reaction mixture was cooled with ice
  5. filtrationthe precipitate was filtered
  6. washThe solid was washed in turn with water (three portions of 20 ml, totaling 60 ml), ethyl ether (20 ml) and n-hexane (50 ml)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-74dd7a6d2a5745ad8c1b248694fc24cf
Source dataset
uspto-grants-1982_08
Patent number
US04347369

Reaction notes

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