3-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chloride → Fluxapyroxad

HRID 1803093Notes

Reaction equation

[F:1][CH:2]([F:12])[C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[F:13][C:14]1[CH:15]=[C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH2:28])[CH:17]=[C:18]([F:21])[C:19]=1[F:20]>C1(C)C=CC=CC=1>[F:13][C:14]1[CH:15]=[C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH:28][C:8]([C:7]2[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=2)=[O:9])[CH:17]=[C:18]([F:21])[C:19]=1[F:20]

Participants

Conditions

Temperature: 85 °C

Procedure

100.0 g (0.504 mol, 98% pure) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride were dissolved at 25° C. in 257.2 g of toluene. The solution was evacuated to 400 mbar and heated to 85° C. Subsequently, within 3 hours, 492.8 g (0.499 mol, 23% strength) of toluenic 3′,4′,5′-trifluorobiphenyl-2-ylamine solution were metered in, after which stirring was continued for another 1 hour. After venting and cooling to 25° C. with a ramp of 10° C./h, the mixture was stirred overnight. Subsequently, the mixture was cooled to 0° C., and the solid constituents were filtered off, washed with cold toluene and dried at 80° C. under reduced pressure. The yield (without further processing of the mother liquor) was 177.7 g (92%).

Workup

customThe solution was evacuated to 400 mbar
waitwas continued for another 1 hour
temperaturecooling to 25° C. with a ramp of 10° C./h
stirringthe mixture was stirred overnight
temperatureSubsequently, the mixture was cooled to 0° C.
filtrationthe solid constituents were filtered off
washwashed with cold toluene
customdried at 80° C. under reduced pressure
customThe yield (without further processing of the mother liquor)

Sources & evidence

ORD record: ord-f8f94c730547442da321dfaecd1155cb
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08350046B2

Reaction notes

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