Aziridine → HCID 9905397, compound

HRID 1058502Notes

Reaction equation

HRID 1058502 reaction equation
[OH:1][CH:2]([CH2:20][OH:21])[CH2:3][NH:4][C:5](=[O:19])[C:6]1[CH:11]=[C:10](Cl)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17].[NH:22]1[CH2:24][CH2:23]1>CCOC(C)=O>[OH:1][CH:2]([CH2:20][OH:21])[CH2:3][NH:4][C:5](=[O:19])[C:6]1[CH:11]=[C:10]([N:22]2[CH2:24][CH2:23]2)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 9033AziridineHCID 10687127HCID 10687127, compound

Product 1

HCID 9905397HCID 9905397, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(2,3-dihydroxypropyl)-5-chloro-2,4-dinitrobenzamide (Friedlos et al., J. Med. Chem., 1997, 40, 1270-1275) (0.50 g, 1.56 mmol) and aziridine (1.00 g, 0.023 mol) in EtOAc (100 mL) was stirred at room temperature for 18 h. After washing with water the solution was worked up to give 2 (0.43 g, 84%): mp (EtOAc/petroleum ether) 145-147° C., 1H NMR [(CD3)2SO] δ8.74 (t, J=5.7 Hz, 1H, NH), 8.64 (s, 1H, H-3), 7.43 (s, 1H, H-6), 4.85 (d, J=4 9 Hz, 1H, OH), 4.58 (t, J=5 7 Hz, 1H, OH), 3 62 (m, 1H, CHOH), 3.44-3.36 (m, 2H, CH2OH), 3.39-3.36 (m, 1H, CONHCHH), 3.16-3.09 (m, 1H, CONHC), 2 48 (s, 4H, aziridine-H); 13C NMR δ164.19 (s), 152.98 (s), 139.70 (s), 138.89 (s), 137 53 (s), 124 57 (d), 122.58 (d), 70.02 (d), 63.70 (t), 42.73 (t), 29.91 (t). Anal. Calcd. for C12H14N4O7. C, 44.18;H, 4.33; N, 17.17%. Found: C, 44.22; H, 4.25; N, 17 40%.

Workup

  1. washAfter washing with water the solution

Sources & evidence

ORD record
ord-d706a6d30db442758fec4d02b9380be1
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

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