2-Chloroaniline → HCID 66863415, compound

HRID 1803095Notes

Reaction equation

HRID 1803095 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:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16]>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][C:8]([C:7]1[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=1)=[O:9]

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chloride

Product 1

HCID 66863415HCID 66863415, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

80.0 g (0.403 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, 221.3 g (0.399 mol, 23% strength) of toluenic 2-chloroaniline solution were metered in and the reaction mixture was stirred for a further 1 hour. After venting and cooling to 20° C. with a ramp of 10° C./h, the mixture was stirred overnight. Subsequently, the mixture was cooled 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 105 g (92%).

Workup

  1. customThe solution was evacuated to 400 mbar
  2. temperaturecooling to 20° C. with a ramp of 10° C./h
  3. stirringthe mixture was stirred overnight
  4. temperatureSubsequently, the mixture was cooled to 0° C.
  5. filtrationthe solids were filtered off
  6. washwashed with cold toluene
  7. customdried at 80° C. under reduced pressure
  8. customThe yield (without further processing of the mother liquor)

Sources & evidence

ORD record
ord-0339bc97253a4b48924b806723e7680a
Source dataset
uspto-grants-2013_01
Patent number
US08350046B2

Reaction notes

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