N-Ethylmaleimide → 2-Azido-n-ethylsuccinimide

HRID 1059488Notes

Reaction equation

HRID 1059488 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]1=[O:9])[CH3:2].[NH:10]=[N+:11]=[N-:12].C1(=O)NC(=O)C=C1>C1(C)C=CC=CC=1>[N:10]([CH:5]1[CH2:6][C:7](=[O:8])[N:3]([CH2:1][CH3:2])[C:4]1=[O:9])=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 4362N-EthylmaleimideHCID 10935Maleimide2×HCID 24530Hydrazoic acid

Product 1

HCID 101763002-Azido-n-ethylsuccinimideYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-30 °C

Procedure

A solution in toluene of N-ethylmaleimide, HN3 (excess relative to the maleimide), and the (salen)AlN3 catalyst depicted above (10 mol % relative to the maleimide) was maintained at −30° C. for 18 h. After a standard quench and work-up of the reaction mixture, the crude material was purified to yield 2-azido-N-ethylsuccinimide (93%, 93% ee).

Workup

  1. customAfter a standard quench
  2. customwork-up of the reaction mixture, the crude material was purified

Sources & evidence

ORD record
ord-6c57a816806d4646804325a4aacefeaa
Source dataset
uspto-grants-2003_02
Patent number
US06521561B1

Reaction notes

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