Hydrochloric Acid → HCID 57904833, compound

HRID 1093037Notes

Reaction equation

HRID 1093037 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[S:12](=[O:14])(=[O:13])[N:11](C(OC)=O)[CH2:10][C:9]2([CH3:20])[CH3:19])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:9]([CH3:20])([CH3:19])[CH2:10][NH:11][S:12]2(=[O:13])=[O:14])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57905214HCID 57905214, compound

Product 1

HCID 57904833HCID 57904833, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a suspension of methyl 5-(4-methoxybenzyl)-4,4-dimethyl-1,2,5-thiadiazolidine-2-carboxylate 1,1-dioxide (17.56 g, 53.5 mmol) in methanol/water (300 mL, 2:1) was added 10 N NaOH (10.7 mL, 107 mmol) and the mixture stirred at room temperature for 4 h. The mixture was made acidic with 10 N HCl and washed with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and concentrated to give the title compound as a white solid (12.91 g, 89% yield). 1H NMR (500 MHz, CDCl3) δ: 7.34-7.32 (2H, m), 6.86-6.84 (2H, m), 4.74 (1H, brs), 4.18 (2H, s), 3.78 (3H, s), 3.24 (2H, s), 1.21 (9H, s).

Workup

  1. washwashed with ethyl acetate
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fa5bddc828e546f7bde88f1031ae5c18
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

Loading…