Dimethylformamide → HCID 136340694, compound

HRID 570967Notes

Reaction equation

HRID 570967 reaction equation
N1CCCCC1.[CH3:7][C:8]1[N:9]=[CH:10][NH:11][C:12]=1[N+:13]([O-:15])=[O:14].[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=O.CN(C=O)C>CC(O)C>[N+:13]([C:12]1[NH:11][CH:10]=[N:9][C:8]=1/[CH:7]=[CH:21]/[C:17]1[S:16][CH:20]=[CH:19][CH:18]=1)([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 73642-ThiophenecarboxaldehydeHCID 8082PiperidineHCID 862781031H-Imidazole, 4-methyl-5-nitro-

Product 1

HCID 136340694HCID 136340694, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

Piperidine (1.7 g, 0.02 mol) was added to a suspension of 4-methyl-5-nitroimidazole (5 g, 0.04 mol) and 2-thiophenecarboxaldehyde (22 g, 0.2 mol) and heated at 100° C. for 15 hours. After cooling, DMF (5 mL) and IPA (15 mL) were added and the precipitate filtered from solution and washed with IPA (50 mL) to leave the product as a yellow solid (6.0 g, 69%). δH (DMSO-d6) 13.56 (1H, bs, NH), 7.90 (1H, s), 7.66 (1H, d, J=16.4), 7.66 (1H, d, J=5.0), 7.40 (1H, d, J=16.4), 7.35 (1H, d, J=3.6), 7.15 (1H, dd, J=3.6, 5.0).

Workup

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

Sources & evidence

ORD record
ord-e935b2b20cf84af9b2f6f47c60e553a9
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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