Dimethylformamide → 2-bromo-1-(2-butynyl)-1H-imidazole-4,5-dicarbonitrile

HRID 501445

Reaction equation

C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:13][C:14]#[C:15][CH3:16].[Br:17][C:18]1[NH:19][C:20]([C:25]#[N:26])=[C:21]([C:23]#[N:24])[N:22]=1>O.C(OCC)(=O)C>[Br:17][C:18]1[N:19]([CH2:13][C:14]#[C:15][CH3:16])[C:20]([C:25]#[N:26])=[C:21]([C:23]#[N:24])[N:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

69.8 g of potassium carbonate and 50 ml N,N-dimethylformamide solution of 74 ml of 1-bromo-2-butyne were added to a 520 ml N,N-dimethylformamide solution of 90.6 g of 2-bromo-1H-imidazole-4,5-dicarbonitrile [CAS No 50847-09-1], and the mixture was heated at 50° C. for 8 hours. 1 L of ethyl acetate and 500 ml of water were added to the solution, and the organic layer was washed twice with 500 ml of water and then with 500 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 48.0 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (1:4).

Workup

washthe organic layer was washed twice with 500 ml of water
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-56faf7657c0340b58029531e17688cc7
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772226B2

Linked notes

Loading…