N-bromobutanimide → HCID 118021566, compound

HRID 518586Notes

Reaction equation

HRID 518586 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-b1d3a8528a9e427b91fd434f5551d9b2
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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