Dimethyl Sulfoxide → HCID 86634051, compound
Reaction equation
F[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH:18]=[O:19].CS(C)=O.C(=O)([O-])[O-].[K+].[K+]>>[CH:18]([C:14]1[N:13]([C:2]2[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH:17]=[CH:16][N:15]=1)=[O:19]Participants
Conditions
- Temperature
- 55 °C
Procedure
Into a Round bottom flask, 2-fluoro-4-nitro-benzonitrile (10.4 g, 0.0624 mol), imidazole-2-carboxaldehyde (5.00 g, 0.0520 mol) and dimethyl sulfoxide (200 mL, 3 mol) were added at room temperature. potassium carbonate (7.19 g, 0.0520 mol) was added portion wise to the reaction mixture and heated at 55° C. for 60 minutes. The reaction was cooled at −20° C. overnight. The content was poured over ice and stirred for 30 minutes. The solid was filtered and washed with water. The resulting solid was dissolved with DCM and washed with Brine. The organic was separated, and dried over magnesium sulfate. The solid was filtered and washed with DCM. The solvent was removed under vacuum to give 2-(2-formyl-imidazol-1-yl)-4-nitro-benzonitrile as a yellow solid (10.48 g, 83%). 1H-NMR (DMSO-D6, 400 MHz): δ9.75 (s, 1H), 8.68 (s, 1H), 8.55 (d, 1H), 8.40 (d, 1H), 7.99 (s, 1H), 7.57 (s, 1H).
Workup
- temperatureThe reaction was cooled at −20° C. overnight
- additionThe content was poured over ice
- filtrationThe solid was filtered
- washwashed with water
- dissolutionThe resulting solid was dissolved with DCM
- washwashed with Brine
- customThe organic was separated
- dry with materialdried over magnesium sulfate
- filtrationThe solid was filtered
- washwashed with DCM
- customThe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-e51a872e74e644e5b7365bf63911c007
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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