Sodium Chloride → HCID 86724835, compound

HRID 929288Notes

Reaction equation

HRID 929288 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](Br)[CH:30]=[CH2:31].[Cl-].[Na+]>C1COCC1>[CH2:31]([O:26][C:16]([C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[CH:7][C:2]=1[Cl:1])([CH:23]([CH3:24])[CH3:25])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1)[CH:30]=[CH2:29]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 71258903HCID 71258903, compound

Product 1

HCID 86724835HCID 86724835, 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 (0.50 g) in 15 mL of THF was added sodium hydride (40 mg) at room temperature. The reaction mixture was then stirred for 30 min followed by the addition of allyl bromide (130 mg) and stirred at room temperature for 18 hours, then at 70° C. for 6 hours and then at 120° C. for 10 hours. An aq. solution of sodium chloride was then added, the mixture was extracted with dichloromethane, dried, evaporated. The crude residue was purified by flash column chromatography on silica gel to give 1-[2-allyloxy-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-butyl]-1,2,4-triazole as a colorless oil (136 mg, 27%; HPLC-MS Rt=1.43 min; masse=432).

Workup

  1. stirringstirred at room temperature for 18 hours
  2. waitat 70° C. for 6 hours
  3. waitat 120° C. for 10 hours
  4. extractionthe mixture was extracted with dichloromethane
  5. customdried
  6. customevaporated
  7. customThe crude residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-dae5ac01c0f049708df3b0648cb19213
Source dataset
uspto-grants-2016_03
Patent number
US09295259B2

Reaction notes

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