3',4'-Dichloro-5-fluoro-[1,1'-biphenyl]-2-amine → Bixafen

HRID 1803096Notes

Reaction equation

HRID 1803096 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.[Cl:13][C:14]1[CH:15]=[C:16]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[NH2:28])[CH:17]=[CH:18][C:19]=1[Cl:20]>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:15]=[C:16]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=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]=[CH:18][C:19]=1[Cl:20]

Participants

4

Reactant 2

HCID 115724193',4'-Dichloro-5-fluoro-[1,1'-biphenyl]-2-amineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chloride

Product 1

HCID 11434448Bixafen

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
85 °C

Procedure

5.6 g (0.029 mol, 98% pure) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride were dissolved at 25° C. in 10.4 g of toluene. The solution was evacuated to 400 mbar and heated to 85° C. Subsequently, within 5 minutes, 7.8 g (0.030 mol, approx. 92% pure) of 3′,4′-dichloro-5-fluorobiphenyl-2-ylamine, dissolved in 28 g of toluene, were metered in and the reaction mixture was stirred for a further 1 hour. After venting and cooling to 25° C. overnight, the mixture was cooled further to 0° C., and the solids 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 8.1 g (71%).

Workup

  1. customThe solution was evacuated to 400 mbar
  2. temperaturecooling to 25° C. overnight
  3. temperaturethe mixture was cooled further to 0° C.
  4. filtrationthe solids were filtered off
  5. washwashed with cold toluene
  6. customdried at 80° C. under reduced pressure
  7. customThe yield (without further processing of the mother liquor)

Sources & evidence

ORD record
ord-c514b2e33d3b4347a6c837cc445ba550
Source dataset
uspto-grants-2013_01
Patent number
US08350046B2

Reaction notes

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