Iodoethane → HCID 71258868, compound

HRID 929289Notes

Reaction equation

HRID 929289 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:16]([OH:26])([CH:23]([CH3:25])[CH3:24])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1.[H-].[Na+].[CH2:29](I)[CH3:30].[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:16]([O:26][CH2:29][CH3:30])([CH:23]([CH3:24])[CH3:25])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1

Participants

6

Reactant 4

HCID 6340Iodoethane2×HCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 71258903HCID 71258903, compound

Product 1

HCID 71258868HCID 71258868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol (2.0 g, 10 mmol) in 50 mL of THF was added sodium hydride (350 mg) at room temperature. The reaction mixture was then stirred for 15 min followed by the addition of ethyliodide (2.39 g, 20 mmol) and stirred at 70° C. for 2 days. After another addition of sodium hydride (350 mg) and ethyliodide (2.39 g, 20 mmol), the mixture was stirred at 70° C. for 1 day more. An aq. solution of ammonium chloride was then added, the mixture was extracted with MTBE, dried, evaporated. The crude residue was purified by flash column chromatography on silica gel to give 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-ethoxy-3-methyl-butyl]-1,2,4-triazole as a colorless oil (75 mg, 3%; HPLC-MS Rt=1.42 min; masse=420).

Workup

  1. stirringstirred at 70° C. for 2 days
  2. stirringthe mixture was stirred at 70° C. for 1 day more
  3. extractionthe mixture was extracted with MTBE
  4. customdried
  5. customevaporated
  6. customThe crude residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-08d3eb150fdc484499a261fa609495a6
Source dataset
uspto-grants-2016_03
Patent number
US09295259B2

Reaction notes

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