Triphenylphosphine → N,N'-di-(t-butoxycarbonyl)-N-(3-nitrophenylmethyl)hydrazine

HRID 1861950Notes

Reaction equation

HRID 1861950 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[N:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[N+:36]([C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42]O)([O-:38])=[O:37]>O1CCCC1>[C:32]([O:31][C:29]([N:20]([CH2:42][C:41]1[CH:44]=[CH:45][CH:46]=[C:39]([N+:36]([O-:38])=[O:37])[CH:40]=1)[NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 692673-Nitrobenzyl alcoholHCID 97268Di-tert-butyl azodicarboxylate

Product 1

HCID 18621947N,N'-di-(t-butoxycarbonyl)-N-(3-nitrophenylmethyl)hydrazineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of triphenylphosphine (2.06 g) in tetrahydrofuran (20 ml), a solution of di-t-butyl azodicarboxylate (1.80 g) in tetrahydrofuran (15 ml) was added dropwise under ice cooling and stirred for 15 min. To the reaction mixture, a solution of m-nitrobenzyl alcohol (1.0 g) in tetrahydrofuran (15 ml) was added dropwise and stirred at room temperature for 63 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1) to give 2.25 g of the titled compound (yield, 94%).

Workup

  1. stirringstirred at room temperature for 63 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b89f98275354457ca4b909881c91bffe
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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