Water → 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[methyl({[(1-phenylethylidene)amino]oxy}carbonyl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile

HRID 644084Notes

Reaction equation

HRID 644084 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH:18][CH3:19])=[C:16]([S:20]([C:22]([F:25])([F:24])[F:23])=[O:21])[C:15]([C:26]#[N:27])=[N:14]1.[C:28](=[N:36][OH:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:29].[CH:38](N(C(C)C)CC)(C)C.C(Cl)(Cl)=O.[OH2:51]>CN(C)C1C=CN=CC=1.O1CCCC1.CCCCCCC.C(OCC)(=O)C.C1(C)C=CC=CC=1>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([N:18]([CH3:38])[C:19]([O:37][N:36]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:29])=[O:51])=[C:16]([S:20]([C:22]([F:25])([F:23])[F:24])=[O:21])[C:15]([C:26]#[N:27])=[N:14]1

Participants

10

Reactant 5

HCID 962WaterHCID 6371PhosgeneHCID 69185AcetophenonoximeHCID 81531DiisopropylethylamineHCID 114308641-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoromethylsulfinylpyrazole

Product 1

HCID 866260671-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[methyl({[(1-phenylethylidene)amino]oxy}carbonyl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a mixture of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoromethylsulfinylpyrazole (0.5 g, 1.1 mmol), acetophenone-oxime (0.165 g, 1.2 mmol), diisopropylethylamine (0.43 g, 3.3 mmol) and 4-dimethylaminopyridine (41 mg, 0.3 mmol) in tetrahydrofuran (15 ml) was added a toluene solution of phosgene (0.66 g, 20%, 1.2 mmol) at 0-5° C. The mixture was stirred at reflux for 2 hours. Extractive workup (heptane-ethyl acetate, water) and chromatography gave the title product (Compound 3-02, 0.14 g) as a solid; 1H-NMR: 2.25 (3H), 3.21 (3H), 7.42 and 7.68 (5H), 7.82 (2H); 19F-NMR: −64.3 (PhCF3); −72.9 (SO—CF3).

Workup

  1. temperatureat reflux for 2 hours

Sources & evidence

ORD record
ord-d1d2b1964fb041528ee5e42d773deb0f
Source dataset
uspto-grants-2010_04
Patent number
US07700639B2

Reaction notes

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