Dimethylformamide → HCID 136340693, compound

HRID 570964Notes

Reaction equation

HRID 570964 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[CH3:11][C:12]1[N:13]=[CH:14][NH:15][C:16]=1[N+:17]([O-:19])=[O:18].N1CCCCC1.CN(C=O)C>CC(O)C>[N+:17]([C:16]1[NH:15][CH:14]=[N:13][C:12]=1/[CH:11]=[CH:7]/[C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 862781031H-Imidazole, 4-methyl-5-nitro-

Product 1

HCID 136340693HCID 136340693, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Cyanobenzaldehyde (75 g, 0.57 mol) was heated to 110° C. Once melted, 4-methyl-5-nitroimidazole (15 g, 0.12 mol) and piperidine (5 g, 0.06 mol) were added and heating continued for a further 24 hours. DMF (15 mL) and IPA (150 mL) were then added and the precipitate filtered from solution and washed with IPA (50 mL) to leave the product as a yellow solid (13.8 g, 49%). mp>300° C. δH (DMSO-d6) 7.95 (1H, s), 7.88 (2H, d, J=6.8), 7.78 (2H, d, J=6.8), 7.78 (1H, d, J=16.8), 7.50 (1H, d, J=16.8); IR (cm−1) 2239 (C≡N), 1502, 1348 (NO2); MS (m/z) 241.1 (C12H9N4O2 (M+1)).

Workup

  1. temperatureheating
  2. filtrationthe precipitate filtered from solution
  3. washwashed with IPA (50 mL)

Sources & evidence

ORD record
ord-53c5770939dc4935932c5089fa8b84e8
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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