N-bromobutanimide → HCID 69491167, compound

HRID 1296736Notes

Reaction equation

HRID 1296736 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)[N:3]=1.[Br:17]N1C(=O)CCC1=O>ClCCl>[Br:17][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[N:3]=[C:2]([CH3:1])[O:6][N:5]=2)=[CH:8][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20800561HCID 20800561, compound

Product 1

HCID 69491167HCID 69491167, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 1b (21 g, 96 mmol) and N-bromosuccinimide (20.5 g, 115 mmol) in dichloromethane (500 mL) was irradiated with a sun lamp for 2 h at rt. The reaction mixture was filtered through a short column of silica gel in dichloromethane and concentrated on a rotary evaporator. The residue was recrystallized (ethyl acetate/hexane/petroleum ether) to afford compound 1c as a white solid (23.2 g, 82%). ESI-MS m/e 300.1 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a short column of silica gel in dichloromethane
  2. concentrationconcentrated on a rotary evaporator
  3. customThe residue was recrystallized (ethyl acetate/hexane/petroleum ether)

Sources & evidence

ORD record
ord-d1841bc380094d35b74e0976ac0d1610
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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