Tetrahydrofuran → HCID 178467482, compound

HRID 280754Notes

Reaction equation

HRID 280754 reaction equation
C([N:4]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]1[CH3:10])(=O)C.[O:11]1CC[CH2:13][CH2:12]1>>[C:12]([C:8]1[NH:4][C:5]([CH3:10])=[N:6][C:7]=1[CH3:9])(=[O:11])[CH3:13]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 13058841HCID 13058841, compound

Product 1

HCID 178467482HCID 178467482, compoundYield 41%

Procedure

A solution of 6.9 g (0.05 M) of 1-acetyl-2,4-dimethylimidazole in 700 ml of dry tetrahydrofuran was photolyzed in a quartz flask with a short wave ultraviolet light source (254 nm) for 40 hours. The tetrahydrofuran solution was concentrated in vacuo to give an oil which was chromatographed on silica gel using 5% methanol in chloroform as eluent to give 2.8 g (41%) of 5-acetyl-2,4-dimethylimidazole as a white solid, mp 83°-87°. Recrystallization from isopropyl ether gave analytically pure material, mp 87°-88°. nmr (CDCl3) (δ): 2.53 (s, 6H); 2.40 (s, 3H). Anal. Calcd. for C7H10N2O: C, 60.85; H, 7.30; N, 20.27; found: C, 60.66; H, 7.26; N, 20.09.

Workup

  1. concentrationThe tetrahydrofuran solution was concentrated in vacuo
  2. customto give an oil which
  3. customwas chromatographed on silica gel using 5% methanol in chloroform as eluent

Sources & evidence

ORD record
ord-4cf1efd5a9ff478e92d69e6376986c86
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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