Dimethylamine → 2,5-Dimethyl-furan-3-carboxylic acid dimethylamide

HRID 2110507Notes

Reaction equation

HRID 2110507 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7](Cl)=[O:8].[CH3:11][NH:12][CH3:13].O1CCOCC1>C1COCC1>[CH3:11][N:12]([CH3:13])[C:7]([C:6]1[CH:5]=[C:4]([CH3:10])[O:3][C:2]=1[CH3:1])=[O:8]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 312751,4-DioxaneHCID 27348042,5-Dimethyl-3-furoyl Chloride

Product 1

HCID 399499902,5-Dimethyl-furan-3-carboxylic acid dimethylamideYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,5-dimethylfuran-3-carbonylchloride (2.19 g; 13.8 mmol) in 10 ml of THF was added to a 2M solution of dimethylamine in dioxane (21 ml; 42 mmol) in 80 ml of THF at rt. After stirring for 1 hr, the volatiles were removed in vacuo and the residue was partitioned between EtOAc (100 ml) and water (100 ml). The organic layer was washed with saturated potassium bisulfate solution (100 ml), 1N NaOH (50 ml) and brine (50 ml). Drying over MgSO4 and concentration in vacuo afforded compound 866A (1.84 g, 80%) as an amber liquid. 1HNMR (CDCl3): δ2.23 (s, 3H), 2.33 (s, 3H), 3.04 (s, 6H), 5.96 (s, 1H).

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe residue was partitioned between EtOAc (100 ml) and water (100 ml)
  3. washThe organic layer was washed with saturated potassium bisulfate solution (100 ml), 1N NaOH (50 ml) and brine (50 ml)
  4. dry with materialDrying over MgSO4 and concentration in vacuo

Sources & evidence

ORD record
ord-414a1444d2dd4d418fc89f4bb01281ea
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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