HCID 18997010, compound → HCID 18996973, compound
Reaction equation
[C:1]([O:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:20][C:21](=[O:23])[CH3:22])[C:10](=[O:24])[C:9]=2[CH:8]=[C:7]([C:25]([NH:27]C(C)(C)C)=O)[CH:6]=1)(=[O:3])[CH3:2]>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:20][C:21](=[O:23])[CH3:22])[C:10](=[O:24])[C:9]=2[CH:8]=[C:7]([C:25]#[N:27])[CH:6]=1)(=[O:3])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
A stirred mixture of 4,5-diacetoxy-9,10-dihydro-N-(1,1-dimethylethyl)-9,10-dioxoanthracene-2-carboxamide (337.0 g) and toluene was warmed to 105° C. and then filtered through a pre-warmed glass sinter funnel. The stirred filtrate was heated back to 100° C. and phosphorus pentachloride (278.0 g) was added portionwise over 15 minutes. The heat was removed and the mixture allowed to cool to room temperature. The mixture was cooled further to 15° C. and the material isolated by filtration and washed in turn with toluene, aqueous sodium bicarbonate (1.5 liters) and water (2×1.5 liters). The green solid was then dried in vacuo at 45° C., m.p. 218°-220° C.
Workup
- filtrationfiltered through a pre-warmed glass sinter funnel
- temperatureThe stirred filtrate was heated back to 100° C.
- additionphosphorus pentachloride (278.0 g) was added portionwise over 15 minutes
- customThe heat was removed
- temperatureto cool to room temperature
- temperatureThe mixture was cooled further to 15° C.
- customthe material isolated by filtration
- washwashed in turn with toluene, aqueous sodium bicarbonate (1.5 liters) and water (2×1.5 liters)
- customThe green solid was then dried in vacuo at 45° C.
Sources & evidence
- ORD record
- ord-103c59ce6c04479a816c33c93925e78b
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05480873
Reaction notes
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