Dimethylformamide → HCID 67037586, compound

HRID 1723659Notes

Reaction equation

HRID 1723659 reaction equation
[CH:1]1([N:5]2[CH:9]=[C:8](C(=O)C)[N:7]=[C:6]2[CH3:13])[CH2:4][CH2:3][CH2:2]1.[CH3:14][C:15]([N:17]([CH3:19])[CH3:18])=O.CN([CH:23]=[O:24])C>>[CH3:18][N:17]([CH3:19])[CH:15]=[CH:14][C:23]([C:9]1[N:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)[C:6]([CH3:13])=[N:7][CH:8]=1)=[O:24]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 31374DimethylacetamideHCID 688810941-Cyclobutyl-2-methyl-4-acetylimidazole

Product 1

HCID 67037586HCID 67037586, compoundYield 47%

Procedure

1-Cyclobutyl-2-methyl-4-acetylimidazole (Method 3; 2.52 g, 14.1 mmol) was dissolved in DMF.DMA (75 mL) and the mixture heated at reflux, under an atmosphere of nitrogen, for 54 hours. The reaction mixture was allowed to cool to ambient temperature the product crystallised. The solid product was collected by filtration, washed with DMF.DMA and then ether and dried under vacuum at 40° C. to give the title compound (1.55 g, 47%) as a pale brown crystalline solid. NMR: 1.72 (m, 2H), 2.28 (m, 2H), 2.39 (s, 3H), 2.64 (m, 2H), 2.95 (m, 6H), 5.22 (m, 1H), 5.50 (d, 1H), 7.39 (s, 1H), 7.51 (d, 1H).

Workup

  1. temperatureat reflux, under an atmosphere of nitrogen, for 54 hours
  2. customcrystallised
  3. filtrationThe solid product was collected by filtration
  4. washwashed with DMF
  5. dry with materialDMA and then ether and dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-0ffa5dac74b64c51b39a39b1efa6292b
Source dataset
uspto-grants-2009_02
Patent number
US07485638B2

Reaction notes

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