Potassium tert-butoxide → HCID 178509547, compound

HRID 1707378Notes

Reaction equation

HRID 1707378 reaction equation
CC(C)([O-])C.[K+].[NH:7]1[CH:11]=[N:10][C:9]([CH:12]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16]Cl)=[N:8]1>O1CCCC1>[C:22]([C:21]1[CH:24]=[CH:25][C:18]([C:12]2([C:9]3[N:10]=[CH:11][NH:7][N:8]=3)[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:19][CH:20]=1)#[N:23]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178509745HCID 178509745, compound

Product 1

HCID 178509547HCID 178509547, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of potassium tert-butoxide (1.10 g) in tetrahydrofuran (50 mL) is added dropwise to a solution of 4-[1-(1,2,4-triazolyl) -5-chloropentyl]benzonitrile (2.50 g) in tetrahydrofuran at 0° (ice-bath). The reaction is allowed to proceed at 0° for 30 minutes and is then allowed to warm to room temperature during 3 hours. The reaction is then quenched with water (100 mL) and the mixture is subsequently extracted with ethyl acetate (100 mL). The organic extract is extracted with 3 N hydrochloric acid (3×30 mL) and the combined acid extracts are made basic with 6 N sodium hydroxide. The crude product is extracted into ethyl acetate (3×30 mL) and the combined extracts are dried (MgSO4) and evaporated to afford 1-(4-cyanophenyl)-1-(1,2,4-triazolyl)cyclopentane. The compound is dissolved in acetone and treated with ethereal HCl to afford the hydrochloride salt.

Workup

  1. customThe reaction is then quenched with water (100 mL)
  2. extractionthe mixture is subsequently extracted with ethyl acetate (100 mL)
  3. extractionThe organic extract
  4. extractionis extracted with 3 N hydrochloric acid (3×30 mL)
  5. extractionThe crude product is extracted into ethyl acetate (3×30 mL)
  6. dry with materialthe combined extracts are dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-22dd19dd86514d3785df0314dc5e5fc0
Source dataset
uspto-grants-1994_10
Patent number
US05352795

Reaction notes

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