Hydrochloric Acid → HCID 22449509, compound
Reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12](N)=[C:11]2[C:6]=1[C:7](=[O:16])[CH2:8][CH2:9][S:10]2)(=[O:3])[CH3:2].N([O-])=O.[Na+].[ClH:21]>O.[Cu]Cl>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]([Cl:21])=[C:11]2[C:6]=1[C:7](=[O:16])[CH2:8][CH2:9][S:10]2)(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Into a solution of 500 mg of 5-acetylamino-8-amino-4-thiochromanone (described in Japanese Patent Laid-open (ko-kai) 279891/1989) suspended in a mixed solvent of 12 ml of concentrated hydrochloric acid and 3 ml of water cooled to 0° C. was slowly dropped a solution of 153 mg of sodium nitrite in 2 ml of water. The mixture was stirred for 5 minutes, whereupon a solution of copper (I) chloride in 3 ml of concentrated hydrochloric acid was added to it at 0° C. The mixture was allowed to stand at room temperature overnight and stirred for 20 minutes at 70° C. The reaction mixture was extracted with chloroform, the extract was dried over anhydrous magnesium sulfate. After concentration, the residue was subjected to silica gel column chromatography using chloroform as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 478 mg of the title compound.
Workup
- additionwas added to it at 0° C
- extractionThe reaction mixture was extracted with chloroform
- dry with materialthe extract was dried over anhydrous magnesium sulfate
- concentrationAfter concentration
- customto obtain fractions
- additioncontaining the target compound
- concentrationThe fractions were concentrated
Sources & evidence
- ORD record
- ord-3ce1924bfb994efe9639a97ba54ce975
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05658920
Reaction notes
Loading…