Hydrochloric Acid → 6-n-Octyloxy-11-methyl-14H-anthra(2,1,9 mna)thioxanthene-14-one
Reaction equation
N[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9][C:10]1[C:11]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:12][C:13]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3C(=O)[C:19]3[C:14]=2[C:15]=1[CH:16]=[CH:17][CH:18]=3.CN([CH:40]=[O:41])C.Cl.N([O-])=O.[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:29]([O:28][C:11]1[CH:12]=[C:13]2[C:26]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:40](=[O:41])[C:19]3[CH:18]=[CH:17][C:16]4[C:2]5[C:3]([S:9][C:10]=1[C:15]=4[C:14]2=3)=[CH:4][CH:5]=[CH:6][C:7]=5[CH3:8])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
70 g (0.14M) of 3-[(2-amino-3-methylphenyl)thio]-2-octyloxy-7H-benzo[de]anthracene-7-one and 1200 ml of DMF were placed into a 2 liter three-necked flask, equipped with a mechanical stirrer and a thermometer. The flask was set onto an ice bath. While stirring, 235 mg of 36% of hydrochloric acid has been added at a temperature not exceeding 20° C. After the reaction mixture was cooled to 0° C., 13.1 g of a sodium nitrite solution in 70 ml of water was added portionwise and held for an hour. Then 0.5 g of copper sulfate (II) has been added at 10° C. and heated till 100° C. The mixture was held for 2 hours, cooled and filtered. The dark red colored precipitate was washed with ethanol and water. The yield=60 g (89. Tm=207-209° C.
Workup
- customequipped with a mechanical stirrer
- customThe flask was set onto an ice bath
- customexceeding 20° C
- waitheld for an hour
- temperatureheated till 100° C
- temperaturecooled
- filtrationfiltered
- washThe dark red colored precipitate was washed with ethanol and water
- customTm=207-209° C.
Sources & evidence
- ORD record
- ord-33e013e936fb4fa9a30fbea89f8ede50
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713636B2
Reaction notes
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