Sodium Methoxide → 5-(4-Chlorophenyl)-4-cyclopropyl-2-{[5-(2,6-dichlorobenzyl)-4H-1,2,4-triazol-3-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714680Notes

Reaction equation

HRID 714680 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[CH2:10][C:11](=[NH:13])[NH2:12].C[O-].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]([CH:29]3[CH2:31][CH2:30]3)[C:27](=[O:32])[N:26]([CH2:33][C:34]([NH:36]N)=O)[N:25]=2)=[CH:20][CH:19]=1>CO>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]([CH:29]3[CH2:31][CH2:30]3)[C:27](=[O:32])[N:26]([CH2:33][C:34]3[NH:12][C:11]([CH2:10][C:4]4[C:3]([Cl:2])=[CH:8][CH:7]=[CH:6][C:5]=4[Cl:9])=[N:13][N:36]=3)[N:25]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12690064(2,6-Dichlorophenyl)ethanimidamide--hydrogen chloride (1/1)HCID 674061412-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide

Product 1

HCID 1785175785-(4-Chlorophenyl)-4-cyclopropyl-2-{[5-(2,6-dichlorobenzyl)-4H-1,2,4-triazol-3-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

58 mg (0.24 mmol) of 2-(2,6-dichlorophenyl)ethaneimidamide hydrochloride were initially charged in 1 ml of dry methanol, 66 μl (0.24 mmol) of a 25% strength methanolic sodium methoxide solution were added and the mixture was stirred at RT for 1 h. 50 mg (0.16 mmol) of the compound from Example 21A, dissolved in 0.6 ml of methanol, were then added. The reaction was stirred at room temperature overnight. The precipitated colorless solid was filtered off with suction, washed with a little methanol and dried under high vacuum. The solid was then suspended in xylene and stirred under reflux for 4 h. After cooling, the mixture was concentrated under reduced pressure and the residue was purified by chromatography [Method 19]. This gave 30 mg (39% of theory) of the target compound as a colorless solid.

Workup

  1. additionwere then added
  2. stirringThe reaction was stirred at room temperature overnight
  3. filtrationThe precipitated colorless solid was filtered off with suction
  4. washwashed with a little methanol
  5. customdried under high vacuum
  6. stirringstirred
  7. temperatureunder reflux for 4 h
  8. temperatureAfter cooling
  9. concentrationthe mixture was concentrated under reduced pressure
  10. customthe residue was purified by chromatography [Method 19]

Sources & evidence

ORD record
ord-99ce65742e014b9ca3f5dbbc543efb3e
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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