Iodoethane → HCID 21984910, compound

HRID 2054553Notes

Reaction equation

HRID 2054553 reaction equation
[C:1]12([C:11]3[N:12]([CH2:17][CH3:18])[C:13]([SH:16])=[N:14][N:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C[O-].[Na+].[CH2:22](I)[CH3:23]>CO>[C:1]12([C:11]3[N:12]([CH2:17][CH3:18])[C:13]([S:16][CH2:22][CH3:23])=[N:14][N:15]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10942334Sodium MethoxideHCID 178462984HCID 178462984, compound

Product 1

HCID 21984910HCID 21984910, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(1 -Adamantyl)-4-ethyl-4H-1,2,4-triazole-3-thiol (D, Arzneim.-Forsch. 1991, 41, 1260-1264) (40 mg, 0.15 mmol) and 0.5 M methanolic NaOMe (0.3 mL, 0.15 mmol) in methanol (1 mL) was heated under reflux for 10 min. Ethyl iodide (12 μl, 0.15 mmol) was added, and the mixture was heated under reflux for 2 h. The methanol was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The organic layer was dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography on silica gel with 10% MeOH in CH2Cl2 to give 3-(1-adamantyl)-4-ethyl-5-(ethylthio)-4H-1,2,4-triazole (2), MS: 278 (M+1).

Workup

  1. temperatureunder reflux for 10 min
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 h
  4. customThe methanol was removed in vacuo
  5. customthe residue was partitioned between CH2Cl2 and water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography on silica gel with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-9eaf05275e5c427b9be2ad4dee862022
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Reaction notes

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