N-Iodosuccinimide → HCID 68858151, compound
Reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([CH3:12])[C:9]([CH3:11])=[CH:10][C:5]=2[N:4]=[CH:3]1.C([Li])(C)(C)C.C1C(=O)N([I:25])C(=O)C1>O1CCCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([CH3:12])[C:9]([CH3:11])=[CH:10][C:5]=2[N:4]=[C:3]1[I:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
In an oven dried nitrogen purged 3 neck 50 mL round bottom flask, 1.00 g (0.624 mmol) of 1,5,6-trimethylbenzimidazole in 2 mL of dry tetrahydrofuran is cooled to −78° C. 0.881 mL (1.498 mmol) of 1.7 M t-butyllithium in hexanes is added and the reaction mixture is stirred at −78° C. for 1 h. 0.154 g (0.686 mmol) of NIS in 2 mL of dry tetrahydrofuran is added. Reaction is removed from bath and stirred at room temperature for 1 hour, quenched with saturated aqueous solution of ammonium chloride, and diluted with dichloromethane. The layers are separated, the aqueous is extracted 3×25 mL dichloromethane, dried (MgSO4), and concentrated. The crude mixture is purified by chromatography using hexanes:ethyl acetate as a solvent system. The product containing fractions are combined to obtain 0.055 g of the title compound, 31% yield. MS, ES+=287.0 (M+1); 1H NMR (DMSO-d6) δ 7.337-7.324 (d, 2H); 3.684 (s, 3H); 2.309 (s, 3H); 2.275 (s, 3H) ppm.
Workup
- customReaction
- customis removed from bath
- stirringstirred at room temperature for 1 hour
- customquenched with saturated aqueous solution of ammonium chloride
- additiondiluted with dichloromethane
- customThe layers are separated
- extractionthe aqueous is extracted 3×25 mL dichloromethane
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe crude mixture is purified by chromatography
- additionThe product containing fractions
Sources & evidence
- ORD record
- ord-91a04baa92d94fdea3313ad6c6a94da3
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557103B2
Reaction notes
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