Diisopropylethylamine → 2-Methylthioethyl [1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinylpyrazol-5-yl]-N-methylcarbamate

HRID 1162854Notes

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(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH3:39][S:40][CH:41](O)[CH3:42].C(N(C(C)C)CC)(C)C.CCCCCCC.[C:60]([O:63]CC)(=[O:62])C>O1CCCC1.CN(C)C1C=CN=CC=1.O>[CH3:39][S:40][CH2:41][CH2:42][O:63][C:60](=[O:62])[N:18]([C:17]1[N:13]([C:3]2[C:4]([Cl:12])=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[Cl:1])[N:14]=[C:15]([C:26]#[N:27])[C:16]=1[S:20]([C:22]([F:23])([F:25])[F:24])=[O:21])[CH3:19]

Participants

Conditions

Temperature: 20 °C

Procedure

To a mixture of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoromethylsulfinylpyrazole (0.60 g, 1.3 mmol) and phosgene-toluene solution (20%, 0.85 g, 1.7 mmol) in tetrahydrofuran (8 ml) was added a solution of methylthioethanol (0.13 g, 1.46 mmol), diisopropylethylamine (0.51 g, 4.0 mmol) and 4-dimethylaminopyridine (0.05 g, 0.4 mmol) in tetrahydrofuran (10 ml) at 0-5° C. The mixture was stirred at 20° C. for 15 hours, then under reflux for 1 hour. Extractive workup (heptane-ethyl acetate, water) and chromatography gave the title product (Compound number 24-02, 0.57 g) as an oil; 1H-NMR: 2.08 (3H); 2.66 (2H); 3.10 (3H); 4.24 (2H); 7.80 (2H); 19F-NMR: −64.3; −72.7 (broad).

Workup

temperatureunder reflux for 1 hour

Sources & evidence

ORD record: ord-e0530a01f32547638ed3754bcd0484b4
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820709B2

Reaction notes

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