Water → 5-Methyl-2-(4-nitrobenzyl)-1,2,5-thiadiazolidine-1,1-dioxide

HRID 1613625Notes

Reaction equation

HRID 1613625 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[CH2:12][CH2:11][NH:10][S:9]1(=[O:14])=[O:13].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)([O-:17])=[O:16].O>CN(C)C=O>[CH3:7][N:8]1[S:9](=[O:14])(=[O:13])[N:10]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 103932802-Methyl-1,2,5-thiadiazolidine 1,1-dioxide

Product 1

HCID 104458805-Methyl-2-(4-nitrobenzyl)-1,2,5-thiadiazolidine-1,1-dioxideYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of anhydrous potassium carbonate (14.49 g, 104.8 mmol) in anhydrous dimethylformamide (80 ml) was added dropwise over 4 minutes a solution of 2-methyl-1,2,5-thiadiazolidine-1,1-dioxide (14 g, 102.8 mmol) in anhydrous dimethylformamide (40 ml), under nitrogen. After 5 minutes, solid 4-nitrobenzyl bromide (22.43 g, 103.8 mmol) was added in one portion and stirring was continued at room temperature for 5 hours. Water (200 ml) was added and products were extracted into ethyl acetate (3×150 ml). The combined organic phases were washed with brine (1×50 ml), dried (Na2SO4) and concentrated. The crude residue was crystallized from ethyl acetate-hexane (70:30) to give 18.31 g (67%) of the title compound as pale yellow crystals. Purification of the mother liquors by flash chromatography (silica gel, hexane-ethyl acetate, 30:70) afforded a further 5.1 g (18.2%) of required product; mp 105°-107° C.; δH (250 MHz, CDCl3) 8.22 (2H, d, J=8.7 Hz, Ar--H), 7.57 (2H, d, J=8.7 Hz, Ar--H), 4.32 (2H, s, Ar--CH2 --), 3.36--3.21 (4H, m, N--CH2CH2 --N), 2.80 (3H, s, --NMe); m/z (CI) 270 (M+ -1).

Workup

  1. waitwas continued at room temperature for 5 hours
  2. extractionproducts were extracted into ethyl acetate (3×150 ml)
  3. washThe combined organic phases were washed with brine (1×50 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was crystallized from ethyl acetate-hexane (70:30)

Sources & evidence

ORD record
ord-2c83a1e3c1f24d6d9a7dc1d708e8f98c
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

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