N-bromobutanimide → HCID 118021566, compound

HRID 575852Notes

Reaction equation

HRID 575852 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]2[CH2:8][CH2:9][CH2:10][C:4]=2[C:3]1=[O:11].C1C(=O)N([Br:19])C(=O)C1>C(#N)C>[Br:19][C:6]1[C:5]2[CH2:8][CH2:9][CH2:10][C:4]=2[C:3](=[O:11])[N:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 14732816HCID 14732816, compound

Product 1

HCID 118021566HCID 118021566, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound of step 6 (140 mg, 1.04 mmol) was dissolved in ACN (5 mL) and NBS (188 mg, 1.06 mmol) was added. After stirring at rt for 1.5 h, purification by silica gel chromatography (PE/EtOAc=1:1) gave the title compound (196 mg, 89.5%) as a white solid. 1H NMR (CD3Cl, 300 MHz): δ 7.33 (s, 1H), 3.53 (s, 3H), 2.85-2.97 (m, 4H), 2.05-2.13 (m, 2H). LCMS: 228, 230 (M+1)+

Workup

  1. custompurification by silica gel chromatography (PE/EtOAc=1:1)

Sources & evidence

ORD record
ord-1fd592006b5e4cdbb50c72b6aae32214
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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