Triethylamine → HCID 10236373, compound

HRID 2054556Notes

Reaction equation

HRID 2054556 reaction equation
[C:1]12([C:11](Cl)=O)CC3CC(CC(C3)[CH2:2]1)C2.FC(F)(F)S(OC)(=O)=O.C1(NC(=S)NN)C=CC=CC=1.C(N(CC)CC)C.[C:41]12([C:51]([NH:53][NH:54][C:55]([NH:57][C:58]3[CH:63]=CC=C[CH:59]=3)=S)=O)[CH2:50][CH:45]3[CH2:46][CH:47]([CH2:49][CH:43]([CH2:44]3)[CH2:42]1)[CH2:48]2>C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:41]12([C:51]3[N:57]([CH:58]4[CH2:59][CH2:63]4)[C:55]([CH:11]4[CH2:1][CH2:2]4)=[N:54][N:53]=3)[CH2:48][CH:47]3[CH2:49][CH:43]([CH2:44][CH:45]([CH2:46]3)[CH2:50]1)[CH2:42]2

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 9526Methyl triflateHCID 989151-Adamantanecarbonyl chlorideHCID 730679Hydrazinecarbothioamide, N-phenyl-HCID 3004969HCID 3004969, compound

Product 1

HCID 10236373HCID 10236373, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(cyclopropyl)cyclopropanecarboxamide (A) (2.08 g, 16.6 mmol) and methyl trifluoromethanesulfonate (1.88 mL, 16.6 mmol) was warmed at 65° in a nitrogen atmosphere. After a few minutes a clear melt was obtained. After 20 min, the melt was cooled and formation of the imino ether triflate salt (B) confirmed by an NMR spectrum. Toluene (26 mL), triethylamine (3.86 mL, 27.7 mmol) and adamantane-1-carbohydrazide (C) (2.15 g, 11.1 mmol) were added, and the two-phase mixture was stirred at 65° for 5 h. The mixture was heated at 110° for 3 h. The cooled reaction was diluted with ethyl acetate (75 mL), washed with water (75 mL) and saturated brine (30 mL), and dried (MgSO4). The ethyl acetate was evaporated in vacuo to give 2.92 g of a yellow syrup. Flash chromatography on silica gel with ethyl acetate eluted the oxadiazole D. Elution with 7% methanol in chloroform and evaporation in vacuo gave crude 4-77. Recrystallization from isopropyl ether afforded pure 3-(1-adamantyl)-4,5-dicyclopropyl-4H-1,2,4-triazole) (4-77). MS: 284 (M+1).

Workup

  1. temperaturewas warmed at 65° in a nitrogen atmosphere
  2. customAfter a few minutes a clear melt was obtained
  3. temperaturethe melt was cooled
  4. temperatureThe mixture was heated at 110° for 3 h
  5. customThe cooled reaction
  6. washwashed with water (75 mL) and saturated brine (30 mL)
  7. dry with materialdried (MgSO4)
  8. customThe ethyl acetate was evaporated in vacuo

Sources & evidence

ORD record
ord-e7dfc9fb311d4b099450a573f07b87b4
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Reaction notes

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