Toluene → 1,2-Bis(4-methoxyphenylmethyl)-4-nitropyrazolidine

HRID 1458288Notes

Reaction equation

HRID 1458288 reaction equation
C1(C)C=CC=CC=1.Cl.Cl.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH:19][NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:14][CH:13]=1.O1CCN([CH2:36][CH:37]([N+:45]([O-:47])=[O:46])[CH2:38]N2CCOCC2)CC1>CO>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:20]2[CH2:38][CH:37]([N+:45]([O-:47])=[O:46])[CH2:36][N:19]2[CH2:18][C:15]2[CH:14]=[CH:13][C:12]([O:11][CH3:10])=[CH:17][CH:16]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6881101,3-Dimorpholino-2-nitropropaneHCID 221019211,2-Bis(4-methoxyphenylmethyl)hydrazine dihydrochloride

Product 1

HCID 130762701,2-Bis(4-methoxyphenylmethyl)-4-nitropyrazolidineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixed solution of toluene (8 ml) and methanol (12 ml) were added 1,2-bis(4- methoxyphenylmethyl)hydrazine dihydrochloride (0.99 g) and 1,3- dimorpholino-2-nitropropane (0.75 g). The mixture was refluxed with heating for 3 hours. The reaction solution was concentrated under a vacuum, purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), thereby yielding 0.88 g (86%) of 1,2-bis (4-methoxyphenylmethyl)-4-nitropyrazolidine.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 3 hours
  3. concentrationThe reaction solution was concentrated under a vacuum
  4. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-fde65eb9267c470fbe579d9bcca65ad1
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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