Water → HCID 21188051, compound

HRID 1383574Notes

Reaction equation

HRID 1383574 reaction equation
[C:1]([C:3]1[C:7]([C:8]#[CH:9])=[C:6]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:5]([C:25]2[C:30]([Cl:31])=[CH:29][C:28]([C:32]([F:35])([F:34])[F:33])=[CH:27][C:26]=2[Cl:36])[N:4]=1)#[N:2].[Br:37]N1C(=O)CCC1=O.CCOCC.O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[C:1]([C:3]1[C:7]([C:8]#[C:9][Br:37])=[C:6]([N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:5]([C:25]2[C:26]([Cl:36])=[CH:27][C:28]([C:32]([F:34])([F:35])[F:33])=[CH:29][C:30]=2[Cl:31])[N:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 21188070HCID 21188070, compound2×

Product 1

HCID 21188051HCID 21188051, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 3-cyano-5-di-(t-butoxycarbonyl)amino-1-(2,6-dichloro-4-trifluoromethylphenyl)4-ethynylpyrazole (100 mg, the compound of Example B4) in acetone (10 ml) was added silver nitrate (5 mg) and N-bromosuccinimide (80 mg). The mixture was stirred at room temperature for one hour and then poured into ether (100 ml) and water (100 ml). The organic layer was separated, dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica gel eluted with dichloromethane to provide the title compound as a pale yellow solid m.p. 130-1° C.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe crude product was purified by column chromatography on silica gel
  5. washeluted with dichloromethane

Sources & evidence

ORD record
ord-0fd74d29617d40caa9b79c9e7353df1a
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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