Iodoethane → HCID 53789918, compound

HRID 1632658Notes

Reaction equation

HRID 1632658 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[CH:17][N:18]([CH3:20])[CH3:19])[C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[CH2:28](I)[CH3:29]>CC(C)=O>[CH2:28]([O:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[CH:17][N:18]([CH3:19])[CH3:20])[C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1)[CH3:29]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10340Sodium Carbonate2×HCID 54215524HCID 54215524, compound

Product 1

HCID 53789918HCID 53789918, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Title product of Example D1 (0.28 g, 1.0 mmole) in 2 ml of acetone was stirred under N2 with Na2CO3 (0.21 g, 2 mmoles) for 1 hour. Ethyl iodide (2.28 ml) and 0.5 g Na2CO3 were then added. The mixture was refluxed for 11 hours, cooled, salts removed by filtration and the filtrate stripped of solvent in vacuo. The residue was chromatographed on silica gel (15 cm×3.5 cm), eluting with 1:1 ethyl acetate:hexane. The resulting oil was crystallized from toluene/pentane to yield purified title product; 51.5 mg; 17%; m.p. 99°-102°.

Workup

  1. temperatureThe mixture was refluxed for 11 hours
  2. temperaturecooled
  3. customsalts removed by filtration
  4. customThe residue was chromatographed on silica gel (15 cm×3.5 cm)
  5. washeluting with 1:1 ethyl acetate
  6. customThe resulting oil was crystallized from toluene/pentane
  7. customto yield
  8. custompurified title product

Sources & evidence

ORD record
ord-d24ca47cc179429c84077554360b205f
Source dataset
uspto-grants-1984_10
Patent number
US04476307

Reaction notes

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