Aziridine → HCID 11266110, compound

HRID 1058511Notes

Reaction equation

HRID 1058511 reaction equation
F[C:2]1[C:3]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[NH:18]1[CH2:20][CH2:19]1>O1CCOCC1>[N:18]1([C:2]2[C:3]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=2)[C:7]([NH2:9])=[O:8])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 9033AziridineHCID 69827687HCID 69827687, compound

Product 1

HCID 11266110HCID 11266110, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred suspension of 5-fluoro-4-(methysulfonyl)-2-nitrobenzamide (Atwell et al., Anti-Cancer Drug Design, 1996, 11, 553-567) (262 mg, 1.00 mmol) in dry dioxane (15 mL) was treated with aziridine (207 μL, 4.00 mmol) at 35° C. for 1 h. The solvent was then removed under reduced pressure, and the residue was shaken with water and recrystallized from MeOH to give 12 (217 mg, 76%) mp 222-224° C., 1H NMR [(CD3)2SO]δ68.39 (s, 1H, H-3), 8.14 & 7 86 (2xbr s, 2H, CONH2), 7.33 (s, 1H, H-6), 3 41 (s, 3H, CH3), 2.57 (s, 4H, aziridine-H). Anal. Calcd for C10H11N3O5S: C, 42.10,H, 3.89, N, 14.73. Found. C, 45.25;H, 3.71; N, 14 98%.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-44a665dc66324ed8bbc0c219534907a5
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

Loading…