N-bromobutanimide → HCID 67384621, compound

HRID 1471922Notes

Reaction equation

HRID 1471922 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[NH:9][N:8]=[CH:7][C:6]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br:16]N1C(=O)CCC1=O>CO>[Br:16][C:7]1[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([CH2:4][CH2:3][O:2][CH3:1])[NH:9][N:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67385401HCID 67385401, compound

Product 1

HCID 67384621HCID 67384621, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(2-methoxyethyl)-4-phenyl-1H-pyrazole (1.0 g, 4.94 mmol) in methanol (20 mL) was added N-bromosuccinimide (0.880 g, 4.94 mmol) in portions at room temperature. After stirred at room temperature for 16 h, the reaction was concentrated and extracted with EtOAc/H2O, purified by column chromatography to give the title compound as yellow oil (1.0 g). LCMS m/z=281.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.97 (t, J=6.63 Hz, 2H), 3.22 (s, 3H), 3.57 (t, J=7.07 Hz, 2H), 7.20-7.27 (m, 2H), 7.35-7.45 (m, 3H), 12.67 (bs, 1H).

Workup

  1. concentrationthe reaction was concentrated
  2. extractionextracted with EtOAc/H2O
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-59e8bb1d3c4f4485bcb40de139aee528
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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