Ethyl isocyanate → N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide

HRID 499996Notes

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[O:13][C:14]1[CH:18]=[C:17]([CH3:19])[NH:16][N:15]=1.[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21]>>[CH2:20]([NH:22][C:23]([N:16]1[C:17]([CH3:19])=[CH:18][C:14]([O:13][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:5][C:4]=2[Cl:12])=[N:15]1)=[O:24])[CH3:21]

Participants

Reactant 2

HCID 8022Ethyl isocyanate

HCID 178623603-(2,6-Dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole

Product 1

HCID 11961271N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamideYield 62.8%

Procedure

3-(2,6-Dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole was reacted with ethyl isocyanate in the same manner as in Example 17 to give a white solid of N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (5.37 g, yield: 62.8%). Melting point: 80˜82° C., 1H-NMR (Acetone-d6, Acetone, ppm): δ1.10 (t, J=7.2 Hz, 3H), 2.55 (d, J=0.8 Hz, 3H), 3.25 (dq, J=6.1 and 7.2 Hz, 2H), 5.71 (q, J=0.8 Hz, 1H), 7.37˜7.48 (brt, 1H, J=6.1 Hz), 7.67 (q, 2H, JHF=0.7 Hz).

Sources & evidence

ORD record: ord-a79974b0791846f1ac2f2606fb1b7ce1
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767827B2

Reaction notes

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