N-bromobutanimide → HCID 15452562, compound

HRID 2297322Notes

Reaction equation

HRID 2297322 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-852e133b39ca4559867c7118d0ef5401
Source dataset
uspto-grants-2002_12
Patent number
USRE037936E1

Reaction notes

Loading…