Bromine → Imazethapyr

HRID 1032822Notes

Reaction equation

HRID 1032822 reaction equation
[C:1]([C:4]([NH:9][CH2:10][C:11]1[N:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].C([O-])(=O)C.[Na+].BrBr>C(O)(=O)C>[CH2:20]([C:17]1[CH:18]=[N:19][C:11]([C:10]2[NH:2][C:1](=[O:3])[C:4]([CH:5]([CH3:7])[CH3:6])([CH3:8])[N:9]=2)=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14])[CH3:21]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 146006872-{[(1-Carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinic acid

Product 1

HCID 54740ImazethapyrYield 51.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.8 g of 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinic acid (2.7 mmol) and 0.56 g sodium acetate (6.8 mmol) in 10 mL acetic acid is warmed until homogeneous and cooled to room temperature. The solution is treated with 0.88 g bromine (5.45 mmol), and the reaction is stirred at 25° C. for 16 hours, then at 75° C. for three days. The reaction mixture is partitioned between CH2Cl2 and water, and the organic phase is dried and concentrated in vacuo. The residue is recrystallized from ethyl acetate-hexanes to afford 0.4 g of the title product having mp 172°-175° C.

Workup

  1. temperatureis warmed until homogeneous and
  2. waitat 75° C. for three days
  3. customThe reaction mixture is partitioned between CH2Cl2 and water
  4. customthe organic phase is dried
  5. concentrationconcentrated in vacuo
  6. customThe residue is recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-1e9af5d8c83a4676a466c359fce1b66a
Source dataset
uspto-grants-1990_09
Patent number
US04959476

Reaction notes

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