N-bromobutanimide → HCID 46832211, compound

HRID 1626174Notes

Reaction equation

HRID 1626174 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[C:14]1[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=1.[Br:20]N1C(=O)CCC1=O>CN(C=O)C>[Br:20][C:15]1[CH:16]=[N:17][N:18]([CH3:19])[C:14]=1[C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][Br:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 46832209HCID 46832209, compound

Product 1

HCID 46832211HCID 46832211, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-[2-(2-bromo-ethoxy)-5-nitro-phenyl]-1-methyl-1H-pyrazole (200 mg, 0.61 mmole), and N-bromosuccinimide (0.61 mmole, 1.0 eq) in 2 mL of DMF was stirred at 100° C. for 10 minutes in the Microwave. The mixture was quenched with water, extract with ethyl acetate, and dried in vacuo give the title compound as a yellow solid (200 mg, 81%). 1H NMR (400 MHz, CDCl3) δ 3.53-3.64 (m, 2H), 3.78 (s, 3H), 4.38-4.49 (m, 2H), 7.11 (d, 1H), 7.57 (s, 1H), 8.23 (s, 1H), 8.39 (d, 1H). Exact mass calculated for C12H11Br2N3O3 402.9, found 406.1 (MH+).

Workup

  1. customThe mixture was quenched with water
  2. extractionextract with ethyl acetate
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e6368d39ff2d4c1ca8f8b6e8c13963ab
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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