Hydrochloric Acid → HCID 59396224, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:4][CH:3]=1.[C:19](Cl)(=[O:23])[C:20](Cl)=[O:21].Cl>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH2:9][N:10]3[C:20](=[O:21])[C:19](=[O:23])[O:12][C:11]32[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
N-[2-(4-chlorophenyl)ethyl]cyclohexanecarboxamide (2.03 g) was dissolved in 1,2-dichloroethane (15 mL), and oxalyl chloride (0.8 mL) was added thereto under ice-cooling. The reaction mixture was stirred at room temperature for 1 hour and then cooled to −20° C. Ferric chloride (1.49 g) was added to the mixture, followed by stirring at room temperature for 16 hours. An aqueous 1 M HCl solution was added to the mixture which was then stirred at room temperature for 30 minutes, followed by extraction with chloroform. The extract was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated and the resulting residue was dried to obtain 9-chloro-10b-cyclohexyl-6,10b-dihydro-5H-[1,3]oxazolo[2,3-a]isoquinoline-2,3-dione (2.38 g).
Workup
- temperatureunder ice-cooling
- temperaturecooled to −20° C
- stirringby stirring at room temperature for 16 hours
- stirringwas then stirred at room temperature for 30 minutes
- extractionfollowed by extraction with chloroform
- washThe extract was washed with water and saturated brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated
- customthe resulting residue was dried
Sources & evidence
- ORD record
- ord-aec0e14f3e0c4b539809e69454623809
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263607B2
Reaction notes
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