Dimethylformamide → 2-n-Butyl-4-chloro-1-(4-bromobenzyl)-5-formylimidazole

HRID 1374138Notes

Reaction equation

[Br:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[CH2:11][C:10](=O)[N:9]=[C:8]2[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O.[OH-].[Na+].CN(C)[CH:28]=[O:29]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[C:11]([CH:28]=[O:29])=[C:10]([Cl:21])[N:9]=[C:8]2[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 115 °C

Procedure

1.61 g of 1-(4-bromo-benzyl)-2-butyl-1,5-dihydroimidazol-4-one and 10 ml of toluene are loaded into a round-bottom flask. The mixture is cooled down to 0–5° C., then added dropwise with 1.4 ml of phosphorous oxychloride. The temperature is slowly allowed to reach 90° C. and 1.2 ml of dimethylformamide are added dropwise. The mixture is heated at 115° C. for 2 h, then cooled to room temperature and added with 50 ml of toluene, 100 g of crushed ice and 10 g of celite. Stirring is continued for 30 minutes, then the pH is adjusted to 8 with 30% aqueous NaOH and the precipitate is filtered off using a Buchner funnel. The organic phase is concentrated under vacuum and chromatographed eluting with 1:1 v/v hexane-diethyl ether. 380 mg of product (IV) as a colourless oil is obtained.

Workup

temperatureThe mixture is cooled down to 0–5° C.
customto reach 90° C.
temperaturecooled to room temperature
filtrationthe precipitate is filtered off
concentrationThe organic phase is concentrated under vacuum
customchromatographed
washeluting with 1:1 v/v hexane-diethyl ether

Sources & evidence

ORD record: ord-9e074e9d265e4433b8d3bd64c0e97e74
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07164029B2

Reaction notes

Loading…