Cyclohexanone → HCID 21188110, compound

HRID 1383586Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[CH:3]=1.[C:21]1(=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C(O)(=O)C.O>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl) pyrazole (1 g, the compound of Reference Example 1 from EP 295,117) and cyclohexanone (1.6 ml) in acetic acid (5 ml) was stirred and heated at 120° C. overnight under an atmosphere of nitrogen. The cooled reaction mixture was diluted with water and extracted with ethyl acetate and then ether. The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution, then water. After drying (MgSO4), evaporation gave the crude product which was purified by column chromatography on silica gel (50 g) eluted with dichloromethane:hexane (1:2), then dichloromethane:hexane (1:1). Combination and evaporation of appropriate fractions provided the title compound as a white solid m.p. 175-7° C.

Workup

customThe cooled reaction mixture
extractionextracted with ethyl acetate
washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution
customAfter drying
custom(MgSO4), evaporation
customgave the crude product which
customwas purified by column chromatography on silica gel (50 g)
washeluted with dichloromethane:hexane (1:2)
customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record: ord-18f4844d6a134949b5721fc5df8f2ab7
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255333B1

Reaction notes

Loading…