Water → HCID 54573799, compound

HRID 1902738Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:16][OH:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+].[Cl:24][C:25]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:26]=1[CH2:27]Cl.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:16][O:17][CH2:27][C:26]1[C:25]([Cl:24])=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:33])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

2 g (0.008 mol) of 1-(2-chloro-4-methylphenyl)-1-oximino-2-(1,2,4-triazol-1-yl)-ethane and 1.2 g (0.008 mol) of potassium carbonate in 8 ml of dimethylformamide were heated to 45° C. and 1.7 g (0.008 mol) of 2,6-dichlorobenzylchloride were added dropwise at that temperature. It was stirred for 12 hours at 60° C., cooled and mixed with 50 ml of water. The mixture was twice extracted with 50 ml of methylene chloride, the combined organic phases were washed with water, dried over sodium sulphate and freed of solvent. The residue which crystallized after some time was recrystallized from ethyl ether/ethyl acetate (1:1). 0.7 g (21% of theory) of 1-(2-chloro 4-methylphenyl)-1-(2,6-dichlorobenzyloximino)-2-(1,2,4-triazol-1-yl)-ethane of melting point 97°-99° C. was obtained.

Workup

temperaturecooled
extractionThe mixture was twice extracted with 50 ml of methylene chloride
washthe combined organic phases were washed with water
dry with materialdried over sodium sulphate
customThe residue which crystallized after some time
customwas recrystallized from ethyl ether/ethyl acetate (1:1)

Sources & evidence

ORD record: ord-996624e128cc48daa9a73d423dda12a5
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04364955

Reaction notes

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