Aziridine → HCID 72536678, compound

HRID 1689592Notes

Reaction equation

HRID 1689592 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2.[N:8]([C:11]1[C:16]([F:17])=[C:15]([F:18])[C:14]([CH:19]=[CH:20][C:21]2[C:25]([CH3:27])([CH3:26])[O:24][C:23](=[C:28]([C:31]#[N:32])[C:29]#[N:30])[C:22]=2[C:33]#[N:34])=[C:13]([F:35])[C:12]=1[F:36])=[N+]=[N-].N1C=CNN1.N1CC1>>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]1[CH:2]2[N:8]1[C:11]1[C:12]([F:36])=[C:13]([F:35])[C:14]([CH:19]=[CH:20][C:21]2[C:25]([CH3:27])([CH3:26])[O:24][C:23](=[C:28]([C:31]#[N:32])[C:29]#[N:30])[C:22]=2[C:33]#[N:34])=[C:15]([F:18])[C:16]=1[F:17]

Participants

5

Reactant 4

HCID 9033Aziridine5×HCID 103522-NorborneneHCID 207464652,3-Dihydro-1H-1,2,3-triazoleHCID 72664996HCID 72664996, compound

Product 1

HCID 72536678HCID 72536678, compound

Procedure

Norbornene (excess amount) and 2-{4-[2-(4-azido-2,3,5,6-tetrafluoro-phenyl)-vinyl]-3-cyano-5,5-dimethyl-5H-furan-2-ylidene}-malononitrile (SM) were mixed together in an NMR tube with CDCl3. The NMR tube was spinning in the NMR instrument and the reaction began instantly. After 5 minutes, some starting material was converted to the dihydrotriazole compound (its structure was identified from its NMR data), which is quite unstable and converted only to the rearrangement product, an aziridine compound at these reaction conditions (the aziridine compound formed here has the same NMR spectrum as the aziridine compound prepared independently). After about 2 h, the starting material was almost gone and the aziridine compound was the main component. After 4 h, the aziridine compound is the only component with some minor byproducts.

Workup

  1. customformed here
  2. customprepared independently)
  3. waitAfter about 2 h
  4. waitAfter 4 h

Sources & evidence

ORD record
ord-481d0cbb54b74478b89a568a5d1ebf22
Source dataset
uspto-grants-2012_04
Patent number
US08153446B2

Reaction notes

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