Iodoethane → HCID 69356079, compound

HRID 852662Notes

Reaction equation

HRID 852662 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[C:15]2[N:14]=[N:13][NH:12][C:11]=2[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[CH:8]=1.[H-].[Na+].[CH2:22](I)[CH3:23]>CN(C=O)C>[CH2:22]([N:12]1[C:11]2[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:7]([N:3]3[CH2:4][CH2:5][CH2:6][C:2]3=[O:1])[C:15]=2[N:14]=[N:13]1)[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178498365HCID 178498365, compound

Product 1

HCID 69356079HCID 69356079, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl methyl 4-(2-oxo-1-pyrrolidinyl)-1H-1,2,3-benzotriazole-6-carboxylate (D249) (400 mg, 1.54 mmol, 1 equiv) in DMF (10 ml) at room temperature was added NaH (60% dispersion in mineral oil, 68 mg, 1.69 mmol, 1.1 equiv) and the resulting mixture was stirred 5 min at this temperature. Ethyl iodide (135 μl, 1.69 mmol, 1.1 equiv) was added and the resulting solution was stirred for 2 h then concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with H2O, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 100/0) gave methyl 1-ethyl-4-(2-oxo-1-pyrrolidinyl)-1H-1,2,3-benzotriazole-6-carboxylate (270 mg, 61%) as a pale yellow oil. [M+H]+=289.3, RT=2.47 min.

Workup

  1. stirringthe resulting solution was stirred for 2 h
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in AcOEt
  4. washthe organic phase was washed with H2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 100/0)

Sources & evidence

ORD record
ord-e7302d7b634242268d13345187b1c2b9
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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