Dimethylformamide dimethyl acetal → 5-(3-Dimethylaminoprop-2-en-1-oyl)-1,2-dimethylimidazole

HRID 1064322Notes

Reaction equation

HRID 1064322 reaction equation
[CH3:1][N:2]([CH3:13])[CH:3]=[CH:4][C:5]([C:7]1[NH:11][C:10]([CH3:12])=[N:9][CH:8]=1)=[O:6].[CH3:14]N(C(OC)OC)C>>[CH3:13][N:2]([CH3:1])[CH:3]=[CH:4][C:5]([C:7]1[N:11]([CH3:14])[C:10]([CH3:12])=[N:9][CH:8]=1)=[O:6]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 14770923-(dimethylamino)-1-(2-methyl-1H-imidazol-5-yl)-2-propen-1-one

Product 1

HCID 693105495-(3-Dimethylaminoprop-2-en-1-oyl)-1,2-dimethylimidazoleYield 29%

Conditions

Temperature
100 °C

Procedure

5-(3-Dimethylaminoprop-2-enoyl)-2-methylimidazole (350 mg, 1.95 mmol) was suspended in DMFDMA (14 ml) and the mixture stirred and heated at 100° C. for 56 hours. The excess DMFDMA was removed by evaporation and the residue purified by chromatography eluting with DCM/MeOH (94:6) to give the title compound 111 mg, (29%) as a solid. NMR (CDCl3): 2.40 (s, 3H), 3.00 (s, 6H), 3.88 (s, 3H), 5.50 (d, 1H), 7.47 (s, 1H), 7.65 (d, 1H); m/z 194.

Workup

  1. customThe excess DMFDMA was removed by evaporation
  2. customthe residue purified by chromatography
  3. washeluting with DCM/MeOH (94:6)

Sources & evidence

ORD record
ord-3889cb8d7a894cf39623f3520a3c7a05
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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