Dimethylformamide → HCID 23287853, compound
Reaction equation
Cl.[Cl:2][C:3]1[CH:31]=[CH:30][C:6]2[O:7][CH2:8][O:9][C:10]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:11]=3[C:12](=CCCN3CCC[C@@H](C(O)=O)C3)[C:5]=2[CH:4]=1.ICI.CN(C)C=[O:38]>>[Cl:2][C:3]1[CH:31]=[CH:30][C:6]2[O:7][CH2:8][O:9][C:10]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:11]=3[C:12](=[O:38])[C:5]=2[CH:4]=1Participants
Conditions
- Temperature
- 105 °C
Procedure
(R)-1-(3-(2,10-Dichloro- 12H-dibenzo[d,g][1,3]-dioxocin-12-ylidene)-1-propyl)-3-piperidinecarboxylic acid hydrochloride ##STR7## 2,2'-Dihydroxy-5,5'-dichlorobenzophenone (12.1 g, 0.042 mol, prepared similarly as described in Journal of the American Chemical Society 77, 543 (1955)) and diiodomethane (11.9 g, 0.044 mol) were dissolved in dry N,N-dimethylformamide (226 ml). Dried and powdered potassium carbonate (8.3 g) was added and the mixture was heated at 105° C. for 5 h and left overnight at room temperature. The reaction mixture was poured on ice (220 g). The precipitate was collected by filtration after 0.5 h and dissolved in diethyl ether (500 ml). The organic layer was washed with 5% sodium hydroxide (50 ml), dried over MgSO4 and evaporated in vacuo, affording 12 g (96%) of 2,10-dichloro-12H-dibenzo[d,g][1,3]-dioxocin-12-one as a solid.
Workup
- customDried
- additionpowdered potassium carbonate (8.3 g) was added
- additionThe reaction mixture was poured on ice (220 g)
- filtrationThe precipitate was collected by filtration after 0.5 h
- dissolutiondissolved in diethyl ether (500 ml)
- washThe organic layer was washed with 5% sodium hydroxide (50 ml)
- dry with materialdried over MgSO4
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-988e0f4cd8df43c49e8c01b1aa036a23
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05753678
Reaction notes
Loading…