Chlorosuccinimide → HCID 15278581, compound

HRID 2395636Notes

Reaction equation

HRID 2395636 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]([CH:19]([CH3:21])[CH3:20])[N:11]=2)=[C:4]([F:22])[CH:3]=1.[Cl:23]N1C(=O)CCC1=O>CN(C)C=O>[Cl:23][C:14]1[C:10]([C:5]2[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[CH:3][C:4]=2[F:22])=[N:11][N:12]([CH:19]([CH3:20])[CH3:21])[C:13]=1[C:15]([F:17])([F:18])[F:16]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 15278580HCID 15278580, compound

Product 1

HCID 15278581HCID 15278581, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1.6 g of 3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-(1-methylethyl)-5-(trifluoromethyl)-1H-pyrazole in 20 mL of dimethylformamide was added 2.0 g of N-chlorosuccinimide. The solution was heated to 80° C. for 2 hours, allowed to cool and poured into ice water. The aqueous mixture was extracted three times with methylene chloride, the combined organic extracts washed with water, dried with MgSO4 and concentrated to give a crude oil. The oil was purified by chromatography and distilled bulb-to-bulb to afford 1.54 g of 4-chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-(1-methylethyl)-5-(trifluoromethyl)-1H-pyrazole as a yellow oil, nD 1.5192 (24° C.).

Workup

  1. temperatureto cool
  2. extractionThe aqueous mixture was extracted three times with methylene chloride
  3. washthe combined organic extracts washed with water
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customto give a crude oil
  7. customThe oil was purified by chromatography
  8. distillationdistilled bulb-to-bulb

Sources & evidence

ORD record
ord-6ccd135e9eea476a944e071df0ab3133
Source dataset
uspto-grants-1996_02
Patent number
US05489571

Reaction notes

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