Triethylamine → 1-(3-nitro-2-pyrazinyl)hexahydro-1H-1,4-diazepin-5-one

HRID 2291018Notes

Reaction equation

HRID 2291018 reaction equation
[NH:1]1[CH2:7][CH2:6][C:5](=[O:8])[NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[N:21][CH:20]=[CH:19][N:18]=1>C(O)(C)C.C(Cl)(Cl)Cl>[N+:23]([C:22]1[C:17]([N:1]2[CH2:7][CH2:6][C:5](=[O:8])[NH:4][CH2:3][CH2:2]2)=[N:18][CH:19]=[CH:20][N:21]=1)([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27372641,4-Diazepan-5-oneHCID 159142352-Chloro-3-nitropyrazine

Product 1

HCID 202293891-(3-nitro-2-pyrazinyl)hexahydro-1H-1,4-diazepin-5-one

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of hexahydro-1H-1,4-diazepin-5-one (1.14 g, 10 mmol) and triethylamine (1.01 g, 10 mmol) in isopropanol (30 ml) cooled in an ice bath, was added over 30 minutes a solution of 2-chloro-3-nitropyrazine (1.59 g, 10 mmol) in chloroform (20 ml). After addition was complete, the reaction mixture was allowed to warm to 20°-25° and was stirred at this temperature for 20 hours. Solvents were removed under reduced pressure and the residue was partitioned between a saturated aqueous solution of sodium chloride and ethyl acetate. The ethyl acetate extract was dried over anhydrous sodium sulfate, filtered and concentrated to an oil. Flash chromatography over silica gel and elution with 2% methanol -98% chloroform gave pure 1-(3-nitro-2-pyrazinyl)hexahydro-1H-1,4-diazepin-5-one. ##STR3##

Workup

  1. additionAfter addition
  2. temperatureto warm to 20°-25°
  3. customSolvents were removed under reduced pressure
  4. customthe residue was partitioned between a saturated aqueous solution of sodium chloride and ethyl acetate
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. washFlash chromatography over silica gel and elution with 2% methanol -98% chloroform

Sources & evidence

ORD record
ord-d71f97324d2b4419b1c9077f5fb58e66
Source dataset
uspto-grants-1986_10
Patent number
US04619927

Reaction notes

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