N-bromobutanimide → HCID 10151356, compound

HRID 1831898Notes

Reaction equation

HRID 1831898 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]([C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]N1C(=O)CCC1=O>ClC(Cl)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]([C:16]2[C:17]([Cl:23])=[CH:18][CH:19]=[CH:20][C:21]=2[Cl:22])[C:11](=[O:24])[C:10]=1[Br:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22050336HCID 22050336, compound

Product 1

HCID 10151356HCID 10151356, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

A mixture of 4-(benzyloxy)-1-(2,6-dichlorophenyl)-6-methylpyridin-2(1H)-one (0.1 g, 0.278 mmol) and N-bromosuccinimide (0.055 g, 0.3 mmol) in dichloroethane (3.0 mL) was stirred at room temperature for 1 h, and heated at 60° C. under argon for 30 min. The reaction mixture was then diluted with dichloroethane (15 mL), washed with water, dried (Na2SO4), filtered, and concentrated under reduced pressure. 1H NMR (CD3OD) δ: 7.64 (m, 2H), 7.55 (m, 3H), 7.38 (m, 3H), 6.65 (s, 1H), 5.34 (s, 2H), and 2.00 (s, 3H); ES-MS m/z=439 (MH+); HR-MS, m/z calc C19H16NO2Cl2Br, 439.9635, found 439.9669.

Workup

  1. temperatureheated at 60° C. under argon for 30 min
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-572bca5e5e074c40b381a0dde1b4e848
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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