Hydrochloric Acid → HCID 85069585, compound
Reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH3:6][CH:7]([NH:14][C:15](=[O:26])[CH2:16][CH2:17][C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12].Cl.O>CO>[NH2:5][C:3]([NH:2][N:1]=[C:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:17][CH2:16][C:15]([NH:14][CH:7]([CH3:6])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[O:26])=[S:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Thiosemicarbazide (1.32 g, 14.5 mmol) was added to a solution of N-(1,5-dimethyl-hexyl)-4-oxo4-phenyl-butyramide (2.54 g, 87.9 mmol), prepared in the previous step, in 30 ml of methanol plus 2.4 ml of 1 N HCl plus 2.4 ml of water and the reaction stirred at room temperature for 48 hours. The reaction was concentrated under reduced pressure to remove the methanol. The residue was partitioned between methylene chloride and water. The organic layer was separated, washed multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 2.95 g of an off-white solid foam. Purification of this foam by chromatography on silica gel (230-400 mesh) using 3:1 hexane-ethyl acetate and then 3:1 ethyl acetate-methylene chloride as the eluted gave the title compound (2.63 g, 82%) as a white foam, mp 58-65° C.
Workup
- concentrationThe reaction was concentrated under reduced pressure
- customto remove the methanol
- customThe residue was partitioned between methylene chloride and water
- customThe organic layer was separated
- washwashed multiple times with water
- dry with materialdried (MgSO4)
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-19a7be4aa4f54fc8a4ed78dd567c15a2
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06316467B1
Reaction notes
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