Tetrahydrofuran → HCID 178509148, compound

HRID 2095186Notes

Reaction equation

HRID 2095186 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-7b5bbdf2dab3432b85ba52674bb20387
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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