Hydrochloric Acid → Ethyl 3-[1-(1,2,3,4-tetrahydronaphthalen-2-yl)imidazol-2-yl-thio]propionate
Reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[CH:15]=[CH:14][NH:13][C:12]1=[S:16].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].Cl>C(O)C>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[S:16][CH2:19][CH2:18][C:17]([O:21][CH2:22][CH3:23])=[O:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydro-imidazole-2-thione (1 g, 4.3 mmol), prepared as in Example 9, ethyl acrylate (4.7 mL, 43 mmol) and hydrochloric acid (1N in ether, 8.7 mL, 8.7 mmol) in 20 mL of ethanol was heated at 80° C. under nitrogen for approximately 5 hours. The mixture was allowed to cool, concentrated and partitioned between saturated sodium bicarbonate solution and methylene chloride. The organic layer was separated and dried (K2CO3), filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (99:1) to give ethyl 3-[1-(1,2,3,4-tetrahydronaphthalen-2-yl)imidazol-2-yl-thio]propionate (1.36 g, 4.1 mmol).
Workup
- temperatureto cool
- concentrationconcentrated
- custompartitioned between saturated sodium bicarbonate solution and methylene chloride
- customThe organic layer was separated
- dry with materialdried (K2CO3)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (99:1)
Sources & evidence
- ORD record
- ord-878cdf037864432290c27ed93dbd6c3d
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719280
Reaction notes
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