Hydrochloric Acid → 2-(4-Aminobenzyl)-5-methyl-1,2,5-thiadiazolidine-1,1-dioxide. Hydrochloride

HRID 1613626Notes

Reaction equation

HRID 1613626 reaction equation
[CH3:1][N:2]1[S:6](=[O:8])(=[O:7])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.C(O)C.C(OCC)(=O)C.[ClH:28]>[Pd].O>[ClH:28].[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[S:6]2(=[O:8])=[O:7])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8857Ethyl AcetateHCID 104458805-Methyl-2-(4-nitrobenzyl)-1,2,5-thiadiazolidine-1,1-dioxide

Product 1

HCID 1317178152-(4-Aminobenzyl)-5-methyl-1,2,5-thiadiazolidine-1,1-dioxide. HydrochlorideYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension of the product from Step 1 (20 g, 74.72 mmol) in a mixture of absolute ethanol (300 ml), ethyl acetate (150 ml), 2N hydrochloric acid (39 ml) and water (25 ml), was hydrogenated at 30 psi for 7 minutes over 10% palladium on carbon (2 g). The catalyst was removed by filtration, washed with ethanol (2×30 ml) and solvents were removed under vacuum. The remaining residue was azeotropically dried with absolute ethanol (1×150 ml) and further dried at high vacuum to give 20.36 g (99.5%) of the required title compound as a white solid. A sample recrystallised from absolute ethanol showed: mp 153°-156° C. (white needles); δH (250 MHz, DMSO-d6) 7.42 (2H, d, J=8.4 Hz, Ar--H), 7.29 (2H, d, J=8.4 Hz, Ar--H), 4.15 (2H, s, Ar--CH2 --N), 3.27--3.17 (4H, m, N--CH2CH2 --N), 2.62 (3H, s, --NMe); m/z (CI) 240 (M+ -1).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol (2×30 ml) and solvents
  3. customwere removed under vacuum
  4. dry with materialThe remaining residue was azeotropically dried with absolute ethanol (1×150 ml)
  5. customfurther dried at high vacuum

Sources & evidence

ORD record
ord-33397f9d105e49c4a63c5324060cdb2d
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

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