N-bromobutanimide → HCID 67306256, compound

HRID 1260171Notes

Reaction equation

HRID 1260171 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH3:24].[Br:25]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[CH:20][CH:21]=2)[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:4][C:3]=1[CH2:24][Br:25]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 67306541HCID 67306541, compound

Product 1

HCID 67306256HCID 67306256, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of tert-butyl N-(4-bromo-3-methylphenyl)-N-(4-cyanophenyl)carbamate (6.18 g, 15.9 mmol), N-bromosuccinimide (2.84 g, 15.96 mmol) and 2,2-azobisisobutyronitrile (0.13 g, 0.798 mmol) in carbon tetrachloride (160 mL) was stirred under nitrogen atmosphere at 95° C. overnight. Then more N-bromosuccinimide (0.566 g, 3.18 mmol) and 2,2-azobisisobutyronitrile was added and the reaction was stirred under nitrogen atmosphere at 95° C. overnight. The reaction mixture was then washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica gel column (9:1 hexane/ethyl acetate) to give tert-butyl N-[4-bromo-3-(bromomethyl)phenyl]-N-(4-cyanophenyl)carbamate.

Workup

  1. stirringthe reaction was stirred under nitrogen atmosphere at 95° C. overnight
  2. washThe reaction mixture was then washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column (9:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3c57517248234b48a322a13fd12c60ed
Source dataset
uspto-grants-2013_06
Patent number
US08470803B2

Reaction notes

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