4-Nitrobenzyl bromide → HCID 10380860, compound

HRID 1613629Notes

Reaction equation

HRID 1613629 reaction equation
[C:1]([N:5]1[CH2:9][CH2:8][NH:7][S:6]1(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)([O-:14])=[O:13]>C(OCC)(=O)C.CCCCCC>[C:1]([N:5]1[CH2:9][CH2:8][N:7]([CH2:19][C:18]2[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)[S:6]1(=[O:10])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 124125142-tert-Butyl-1lambda~6~,2,5-thiadiazolidine-1,1-dione

Product 1

HCID 10380860HCID 10380860, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared in 70% yield from 2-tert-butyl-1,2,5-thiadiazolidine-1,1-dioxide [M. Preiss, Chem. Ber., 1978, 111, 1915] and 4-nitrobenzyl bromide following the procedure described for Example 1 (Method B, Step 1); mp 113° C. (ethyl acetate-hexane, 60:40); δH (360 MHz, CDCl3) 8.21 (2H, d, J=8.7 Hz, Ar--H), 7.58 (2H, d, J=8.7 Hz, Ar--H), 4.24 (2H, s, Ar--CH2 --), 3.40 (2H, t, J=6.2 Hz, --CH2 --), 3.17 (2H, t, J=6.2 Hz, --CH2 --), 1.44 (9H, t-Bu); m/z (EI) 313 (M+).

Sources & evidence

ORD record
ord-74869576b9c24d469de30030ff51a7a4
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

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