Ethyl Acetate → HCID 9837675, compound

HRID 1058515Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([N+:11]([O-])=O)[C:3]=1[N+:14]([O-:16])=[O:15].[C:17](OCC)(=O)[CH3:18]>>[N:11]1([C:4]2[C:3]([N+:14]([O-:16])=[O:15])=[C:2]([Cl:1])[CH:10]=[CH:9][C:5]=2[C:6]([NH2:8])=[O:7])[CH2:18][CH2:17]1

Participants

Reactant 2

HCID 8857Ethyl Acetate

HCID 18668167HCID 18668167, compound

Product 1

HCID 9837675HCID 9837675, compound

Procedure

Reaction of 4-chloro-2,3-dinitrobenzamide [Goldstein and Schaaf, Helv. Chim. Acta. 1957, 40, 369-376] in ethyl acetate generally as described in Example L, except that the reaction time was 3 hours, gave 2-(aziridin-1-yl)-4-chloro-3-nitrobenzamide (16) as a yellow powder, mp 216° C. 1H NMR [(CD3)2SO] δ8 16 (br s, 1H CONHH), 7 71 (br s, 1H, CONHH), 7 69 (d, J=8.3 Hz, 1H, H-6), 7.25 (d, J=8.3 Hz, 1H, H-5), 2.28 (s, 4H, aziridine-H) 13C NMR δ165.53 (s), 142.59 (s), 142.49 (s), 131 65 (d), 129.71 (s), 129.00 (s), 121.37 (d), 29.40 (t). Found. C, 44.90;H, 3.49; N, 17.39. C9H8ClN3O3 requires C, 44.73;H, 3.33; N, 17.39%.

Sources & evidence

ORD record: ord-9104763d86814058a75cb3cf58e78603
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06517836B1

Reaction notes

Loading…