Tetrahydrofuran → HCID 10220418, compound

HRID 1058514Notes

Reaction equation

[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([N+:14]([O-])=O)[CH:3]=1.O1CC[CH2:19][CH2:18]1>>[N:14]1([C:4]2[CH:3]=[C:2]([Cl:1])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]=2[C:6]([NH2:8])=[O:7])[CH2:19][CH2:18]1

Participants

Reactant 2

HCID 8028Tetrahydrofuran

HCID 18668169HCID 18668169, compound

Product 1

HCID 10220418HCID 10220418, compound

Procedure

Reaction of 4-chloro-2,5-dinitrobenzamide [Goldstein and Schaaf, Helv. Chim Acta. 1957, 40, 369-376] in tetrahydrofuran as described in Example C except that the reaction time was 2 hours, gave 2-(aziridin-1-yl)-4-chloro-5-nitrobenzamide (15) as a yellow powder, mp 155° C. 1H NMR [(CD3)2SO] δ8.15 (s, 1H, H-6), 7.83, 7 81 (2 br s, 2H, CONH2), 7.40 (s, 1H, H-3),2.33 (s, 4H, aziridin-H). 13NMR δ165.68 (s), 156 66 (s), 140.39 (s), 128 46 (s), 127 87 (s), 127 02 (d), 123.94 (d), 29.35 (t). Found: C,44.70;H, 3.14; N, 17.41. C9H8ClN3O3 requires C, 44 73;H, 3.33; N, 17.39%

Sources & evidence

ORD record: ord-0f604688730d4aa1880e6ed0509dac3c
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06517836B1

Reaction notes

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