Iodoethane → HCID 12051933, compound

HRID 1871929Notes

Reaction equation

HRID 1871929 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[C:13]2[N:21]=[N:20][N:19]([CH2:22][CH2:23][CH3:24])[C:14]=2[N:15]=[C:16]([CH3:18])[N:17]=1.[H-].[Na+].[CH2:27](I)[CH3:28]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:27][CH3:28])[C:12]1[C:13]2[N:21]=[N:20][N:19]([CH2:22][CH2:23][CH3:24])[C:14]=2[N:15]=[C:16]([CH3:18])[N:17]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12051932HCID 12051932, compound

Product 1

HCID 12051933HCID 12051933, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound from Example 1 (0.30 g) was dissolved in dry DMF (10 mL) and added NaH (62 mg; 60% in oil) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 5 mins., and then added EtI (0.2 mL) and continued for an additional 24 h. The reaction mixture was partitioned between ethyl acetate (25 mL) and water (25 mL), washed the organic layer with brine, dried, and stripped in vacuum to yield a pale yellow oil. The sample was purified by flash column chromatography (1:100 MeOH +CH2Cl2) to afford the title compound as a colorlesss oil (0.16 g). Elemental analysis for C19H25BrN6 : Theory C: 54.68, H: 6.05 Found: C: 54.66, H: 6.02.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (25 mL) and water (25 mL)
  2. washwashed the organic layer with brine
  3. customdried
  4. customto yield a pale yellow oil
  5. customThe sample was purified by flash column chromatography (1:100 MeOH +CH2Cl2)

Sources & evidence

ORD record
ord-b22e2d18eb104585960101487f34cc7f
Source dataset
uspto-grants-2000_08
Patent number
US06107300

Reaction notes

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