N-bromobutanimide → HCID 9890693, compound

HRID 1274353Notes

Reaction equation

HRID 1274353 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1[CH:25]=[CH:24][O:23][CH:22]=1.[Br:26]N1C(=O)CCC1=O>O1CCCC1>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:17])([F:15])[F:16])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1[CH:25]=[CH:24][O:23][C:22]=1[Br:26]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 221209065-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(3-furanyl)pyrazole

Product 1

HCID 9890693HCID 9890693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(furan-3-yl)pyrazole (0.600 g) in tetrahydrofuran (20 ml) was added N-bromosuccinimide (0.288 g). The mixture was left at room temperature for 2 hours and then poured onto a column of silica gel (30 g) and eluted with hexane:dichloromethane (1:1). Combination and evaporation of suitable fractions gave a red oil which was further purified by column chromatography on silica gel (30 g) eluted with hexane:dichloromethane (1:1), then dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a white solid.

Workup

  1. additionpoured onto a column of silica gel (30 g)
  2. washeluted with hexane:dichloromethane (1:1)
  3. customCombination and evaporation of suitable fractions
  4. customgave a red oil which
  5. customwas further purified by column chromatography on silica gel (30 g)
  6. washeluted with hexane:dichloromethane (1:1)
  7. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-411f88d44a5b4b56aa8f4a5a39686a3c
Source dataset
uspto-grants-2000_12
Patent number
US06156782

Reaction notes

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