N-bromobutanimide → HCID 67384644, compound

HRID 1471881Notes

Reaction equation

HRID 1471881 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1.[Br:16]N1C(=O)CCC1=O>CO>[Br:16][C:6]1[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][NH:9][C:5]=1[CH2:4][CH2:3][S:2][CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67384813HCID 67384813, compound

Product 1

HCID 67384644HCID 67384644, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(2-(methylthio)ethyl)-3-phenyl-1H-pyrazole (4.0 g, 18.32 mmol) in methanol (20 mL) was added N-bromosuccinimide (3.26 g, 18.32 mmol) slowly at 0° C. The reaction was stirred at 0° C. for 2 h. The mixture was concentrated and purified by silica gel column chromatography to give the title compound (3.4 g). LCMS m/z=297.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.11 (s, 3H), 2.79 (t, J=7.83 Hz, 2H), 2.83-2.97 (m, 2H), 7.32-7.56 (m, 3H), 7.67-7.88 (m, 2H), 13.20 (bs, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e5089cd9b48244278ed8b775fe79be14
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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