Ethanol → 5-{4-[(3-Isopropyl-1H-indol-5-yl)oxy]-3,5-bis-trifluoromethylphenyl}-imidazolidin-2,4-dione

HRID 1007511Notes

Reaction equation

[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][C:17](C=O)=[CH:16][C:15]=3[C:26]([F:29])([F:28])[F:27])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2].[C-:30]#[N:31].[Na+].[C:33](=[O:36])([O-])[O-].[NH4+:37].[NH4+].[CH2:39]([OH:41])C>O>[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:21]([C:22]([F:24])([F:23])[F:25])=[CH:20][C:17]([CH:30]4[NH:31][C:39](=[O:41])[NH:37][C:33]4=[O:36])=[CH:16][C:15]=3[C:26]([F:27])([F:28])[F:29])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

3.0 g (7.22 mmol) of aldehyde from Example V dissolved in 30 ml of ethanol are added to a solution of 0.581 g (14.4 mmol) of sodium cyanide and 3.63 g (36.1 mmol) of ammonium carbonate in 30 ml of water and the mixture is stirred for 24 hours at 60° C. Ethanol is then distilled off from the reaction solution, it is diluted with water, acidified to pH 2 with 1N hydrochloric acid with ice-cooling and extracted twice with ethyl acetate. After drying and distilling off the solvent, the crude product (4.03 g) is chromatographed on silica gel 60 using methylene chloride with addition of a little methanol in the ratio 20:1 to 20:2.5.

Workup

distillationEthanol is then distilled off from the reaction solution, it
additionis diluted with water
temperaturecooling
extractionextracted twice with ethyl acetate
customAfter drying
distillationdistilling off the solvent
customthe crude product (4.03 g) is chromatographed on silica gel 60 using methylene chloride with addition of a little methanol in the ratio 20:1 to 20:2.5

Sources & evidence

ORD record: ord-4a5ea915a5a34698882c09cd6dfeef0a
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794406B2

Reaction notes

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