N-bromobutanimide → HCID 15452562, compound

HRID 582270Notes

Reaction equation

HRID 582270 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:5]=[C:4]([Cl:18])[C:3]=1[N:19]1[C:23]([NH2:24])=[CH:22][C:21]([C:25]#[N:26])=[N:20]1.[Br:27]N1C(=O)CCC1=O>C(#N)C>[Cl:18][C:4]1[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:17])[F:16])=[CH:12][CH:13]=2)[CH:7]=[C:2]([Cl:1])[C:3]=1[N:19]1[C:23]([NH2:24])=[C:22]([Br:27])[C:21]([C:25]#[N:26])=[N:20]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15452561HCID 15452561, compound

Product 1

HCID 15452562HCID 15452562, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1-[2,6-dichloro-4-(4-trifluoromethylphenyl)phenyl]-3-cyano-5-aminopyrazole (1 g), N-bromosuccinimide (0.5 g) and acetonitrile was stirred at 20° C. for 90 minutes, then concentrated and the residue was mixed with diethyl ether, washed with saturated aqueous NaHCO3 solution, dried, filtered and the filtrate concentrated and purified via chromatography. The desired product as a solid (1.04 g, mp 178-180° C.) was obtained.

Workup

  1. concentrationconcentrated
  2. additionthe residue was mixed with diethyl ether
  3. washwashed with saturated aqueous NaHCO3 solution
  4. customdried
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated
  7. custompurified via chromatography

Sources & evidence

ORD record
ord-5860c9f174c547c19f33d2182e74d7c0
Source dataset
uspto-grants-1999_07
Patent number
US05922884

Reaction notes

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