Dimethyl Sulfoxide → HCID 12067747, compound
Reaction equation
CS(C)=O.[NH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>C(N(CC)CC)C>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:5][CH2:6][CH2:7][CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:16][CH:17]=1)([O-:23])=[O:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
100 ml of DMSO were introduced into a 500 ml three-necked flask and treated with 10.3 g of triethylamine, 12.8 g of 1-(3-aminopropyl)imidazole and 14.4 g of 1-fluoro-4-nitrobenzene. The mixture was stirred at 80° C. for 12 h, cooled to room temperature and subsequently poured onto 1 l of ice. A sample of the resulting oily precipitate was triturated with H2O until crystallization commenced. A sample of the mixture was seeded with the crystals thus obtained and crystallized at room temperature for 1 h. The resulting precipitate was filtered off with suction, triturated with H2O, filtered off with suction again and rewashed with H2O. For the purpose of purification, the 28 g of moist crude product thus obtained were recrystallized from 250 ml of H2O and 114 ml of ethanol. The product was dried in vacuo at 50° C.
Workup
- temperaturecooled to room temperature
- customA sample of the resulting oily precipitate was triturated with H2O until crystallization
- customthus obtained
- customcrystallized at room temperature for 1 h
- filtrationThe resulting precipitate was filtered off with suction
- customtriturated with H2O
- filtrationfiltered off with suction again
- customFor the purpose of purification
Sources & evidence
- ORD record
- ord-2f1ef429b3c44887b59ac94f97264e8c
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07081140B2
Reaction notes
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