Ethanol → HCID 23070778, compound
Reaction equation
[NH4+]=[S:2].C(O)C.[CH2:6]([N:10]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([C:20]#[N:21])[N:12]=[C:11]1[N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)[C:7]#[C:8][CH3:9].C(OCC)(=O)C>O>[CH2:6]([N:10]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([C:20](=[S:2])[NH2:21])[N:12]=[C:11]1[N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH2:24][CH2:23]1)[C:7]#[C:8][CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
5 ml of an aqueous solution of 50% ammonium sulfide was added to a 20-ml ethanol solution containing 0.80 g of t-butyl 4-[1-(2-butynyl)-4-cyano-5-ethoxycarbonyl-1H-imidazol-2-yl]piperazine-1-carboxylate, and the mixture was heated at 60° C. for 14 hours. 100 ml of ethyl acetate and 50 ml of water were added to the mixture, and the organic layer was washed successively with 50 ml of water and 50 ml of a saturated sodium chloride solution. The reaction solution was dried over anhydrous magnesium sulfate, then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.58 g of the title compound was obtained from the fraction eluted with hexane-ethyl acetate (3:2).
Workup
- washthe organic layer was washed successively with 50 ml of water and 50 ml of a saturated sodium chloride solution
- dry with materialThe reaction solution was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-5e8d2d8e8d8045d581c5d5ebc2243156
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772226B2
Reaction notes
Loading…