Water → HCID 86748266, compound

HRID 2380269Notes

Reaction equation

[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:17]=[CH:18][CH:19]=1)[C:9]([N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)=[N:10][OH:11].[H-].[Na+].I[CH:25]([CH3:27])[CH3:26].O>CN(C)C=O>[CH:25]([O:11][N:10]=[C:9]([N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)[C:8]1[CH:17]=[CH:18][CH:19]=[C:6]([O:5][CH2:4][CH2:3][C:2]([CH3:21])([CH3:20])[CH3:1])[CH:7]=1)([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1.6 g (5.6 mmol) of 1-[3-(3,3-dimethylbutoxy)benzohydroximoyl]-1H-1,2,4-triazole dissolved in 100 ml of N,N-dimethylformamide was added 0.16 g (6.7 mmol) of sodium hydride. The mixture was stirred for 20 minutes at 80° C. And then allowed to sit and cool naturally to about 50° C. To the mixture was added 1.1 g (6.5 mmol) of 2-iodopropane and stirred for 1 hour at about 50° C. The reaction mixture was allowed to sit and cool naturally to room temperature. The cooled mixture was poured into water and extracted with ethyl acetate. After being washed with water, the organic layer was dried over anhydrous magnesium sulfate. The solvent in the organic layer was removed under reduced pressure. The residue was purified by column chromatography, thus obtaining 1.4 g (yield: 87%) of the desired product having a refractive index of [nD20 ] 1.5289 at 20° C.

Workup

temperaturecool naturally to about 50° C
stirringstirred for 1 hour at about 50° C
temperaturecool naturally to room temperature
extractionextracted with ethyl acetate
washAfter being washed with water
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
customThe solvent in the organic layer was removed under reduced pressure
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-9ae3580bdc81436ba17e63574872186b
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05366988

Reaction notes

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