p-Fluoronitrobenzene → 4-(5-Benzyl-1,1-dioxo-1,2,5-thiadiazolidin-2-yl)nitrobenzene

HRID 1613637Notes

Reaction equation

HRID 1613637 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][NH:10][S:9]1(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>>[CH2:1]([N:8]1[S:9](=[O:14])(=[O:13])[N:10]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH2:11][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 103758902-Benzyl-1,2,5-thiadiazolidine 1,1-dioxide

Product 1

HCID 103147634-(5-Benzyl-1,1-dioxo-1,2,5-thiadiazolidin-2-yl)nitrobenzeneYield 79%

Procedure

The title compound was prepared in 79% yield from 2-benzyl-1,2,5-thiadiazolidine-1,1-dioxide and 1-fluoro-4-nitrobenzene using a similar method to that described for Example 20 (step 1). The crude product was crystallised from ethyl acetate to give a yellow solid; mp 164°-165° C.; δH (360 MHz, DMSO-d6) 8.30 (2H, d, J=9.2 Hz, Ar--H), 7.40 (5H, m, Ph), 7.33 (2H, d, J=9.2 Hz, Ar--H), 4.31 (2H, s, PhCH2 --), 3.98 (2H, t, J=6.4 Hz, --CH2 --), 3.49 (2H, t, J=6.4 Hz, --CH2 --); m/z (EI) 333 (M+).

Workup

  1. customThe crude product was crystallised from ethyl acetate
  2. customto give a yellow solid

Sources & evidence

ORD record
ord-1293d0aa78ac451b9e4d0b4ca5a28bd6
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

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