D-Glucosamine → 1-(1,2,3,4-Tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione
Reaction equation
[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)=[C:2]=[S:3].O[CH:15]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H:16]1[NH2:17]>C(O)(=O)C>[CH2:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][CH2:13][CH:4]1[N:1]1[CH:15]=[CH:16][NH:17][C:2]1=[S:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 2-isothiocyano-1,2,3,4-tetrahydronaphthalene (1.89 g, 10 mmol), prepared as in Example 10, and D-(+)-glucosamine (1.78 g, 10 mmol) was stirred at 90° C. until homogenous and then 0.8 mL of acetic acid was added. The mixture was stirred at 90° C. for 30 minutes and then cooled. The solvents were removed by rotary evaporation and the residue was co-evaporated with toluene (2×25 mL). The residue was dissolved in acetic acid and heated at 90° to 100° C. for 30 minutes. The mixture was cooled and triturated with acetone giving a crystalline material. The material was isolated by filtration and the filter residue washed with acetone. Drying gave 4-(1R,2R,3S,4)-tetrahydroxybut-1-yl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (1.48 g, 4.23 mmol).
Workup
- additionwas added
- temperaturecooled
- customThe solvents were removed by rotary evaporation
- dissolutionThe residue was dissolved in acetic acid
- temperatureheated at 90° to 100° C. for 30 minutes
- temperatureThe mixture was cooled
- customtriturated with acetone giving a crystalline material
- customThe material was isolated by filtration
- washthe filter residue washed with acetone
- customDrying
Sources & evidence
- ORD record
- ord-d328838e28954a6a9f4a8148db13b066
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05538988
Reaction notes
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