2-Methylaziridine → N,N'-Hexamethylenebis(2-methyl-1-aziridinecarboxamide)

HRID 2402486Notes

Reaction equation

HRID 2402486 reaction equation
[CH3:1][CH:2]1[CH2:4][NH:3]1.[N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]=[C:15]=[O:16])=[C:6]=[O:7]>C1(C)C=CC=CC=1>[CH2:13]([NH:14][C:15]([N:3]1[CH2:4][CH:2]1[CH3:1])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][NH:5][C:6]([N:3]1[CH2:4][CH:2]1[CH3:1])=[O:7]

Participants

4

Reactant 2

HCID 63772-MethylaziridineHCID 13192Hexamethylene diisocyanate

Product 1

HCID 97887N,N'-Hexamethylenebis(2-methyl-1-aziridinecarboxamide)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Methyl aziridine (15.05 grams, 0.26 moles) was added drop wise over one hour to a solution of 1,6-diisocyanatohexane (20.00 grams, 0.12 moles, Aldrich) in toluene (40 mL) while cooling in an ice bath. After stirring for a total of 24 hours at room temperature, a potion of the solvent was removed under vacuum to give N,N′-(hexane-1,6-diyl)bis-(2-methylaziridine-1-carboxamide)

Workup

  1. temperaturewhile cooling in an ice bath
  2. customa potion of the solvent was removed under vacuum

Sources & evidence

ORD record
ord-f11258f252a5408ab43c6953d35ae18c
Source dataset
uspto-grants-2014_08
Patent number
US08796390B2

Reaction notes

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