Iodoethane → HCID 90240104, compound

HRID 1051906Notes

Reaction equation

HRID 1051906 reaction equation
[Br:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([Br:15])[C:9]([Br:14])=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=2[N:3]=1.[OH-].[Na+].I[CH2:19][CH3:20]>C(#N)C>[Br:1][C:2]1[N:6]([CH2:19][CH3:20])[C:5]2[CH:7]=[C:8]([Br:15])[C:9]([Br:14])=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 90242331HCID 90242331, compound

Product 1

HCID 90240104HCID 90240104, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

2,5,6-tribromo-4-nitro-1H-1,3-benzodiazole (Method 2) (28 mmol, 10 g) was dissolved in acetonitrile (200 ml), and then NaOH (33.8 mmol, 1.35 g) was added. The resulting mixture was stirred at temperature for 0.5 h. Next 2-iodoethane (225 mmol, 35.16 g) was added, and the mixture was heated to 85° C. until the reaction was complete (20 h) by LC/MS. The mixture was allowed to cool to RT and concentrated in-vacuo. The product was taken up into ethyl acetate and washed with water. The organic extract was dried over MgSO4, filtered and concentrated. The product was purified on silica gel using EA/hex (1:1) to afford compound 2,5,6-tribromo-1-ethyl-4-nitro-1H-1,3-benzodiazole (mg). 1H NMR (600 MHz, DMSO) δ 8.58 (s, 1H), 4.36 (q, J=7.2 Hz, 2H), 1.33 (t, J=7.2 Hz, 3H); m/z 427.8; rt 3.5 min.

Workup

  1. custom(20 h)
  2. temperatureto cool to RT
  3. concentrationconcentrated in-vacuo
  4. washwashed with water
  5. extractionThe organic extract
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified on silica gel

Sources & evidence

ORD record
ord-a4c99dac668146ebb446bb846cc6134c
Source dataset
uspto-grants-2016_07
Patent number
US09388192B2

Reaction notes

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