Tetrahydrofuran → HCID 178509148, compound

HRID 255020Notes

Reaction equation

HRID 255020 reaction equation
[N:1]1([CH2:7][CH2:8][C:9](=O)[C:10](=[N:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]#[N:12])CCOCC1.O.[NH2:23][NH2:24].[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1.NN>C(OCC)C>[N:1]1([CH2:7][CH2:8][C:9]2[C:10](=[N:13][NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]([NH2:12])=[N:23][N:24]=2)[CH2:25][CH2:29][O:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 86601975HCID 86601975, compound

Product 1

HCID 178509148HCID 178509148, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 5-morpholin-4-yl-3-oxo-2-(phenylhydrazono)pentanenitrile (1.2 mmole) in 15 mL of diethyl ether was slowly added a solution of hydrazine hydrate (2.4 mmol) in 2 of THF which resulted in a clear red solution. After 2 hours, another portion of hydrazine (2.4 mmol) was added at which point some yellow precipitate was observed. The reaction was stirred at ambient temperature overnight. The solid was collected by filtration, purified by recrystalization from ethanol and dried in vacuo to yield 150 mg (41%) of the title compound. MS (m/z, ES+): 301 (M+1, 100%). 1H NMR (ppm, 300 MHz, DMSO-d6) δ 11.63 (br s, 1H), 7.67 (m, 2H), 7.44 (m, 2H), 7.29 (m, 1H), 6.97 (br s, 2H), 3.55 (m, 4H), 2.93 (m, 2H), 2.66 (m, 2H), 2.43 (m, 4H).

Workup

  1. customresulted in a clear red solution
  2. filtrationThe solid was collected by filtration
  3. custompurified by recrystalization from ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-88eee1573dfe41ebad89600a8c2c64a8
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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